Compendium of Organic Synthetic Methods
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About this ebook
The Compendium of Organic Synthetic Methods serves as a handy desktop reference for organic chemists to browse new reactions and transformations of interest, facilitating the search for functional group transformations in the original literature of organic chemistry. Volume 13 contains both functional group transformations and carbon-carbon bond forming reactions from the literature in the years 2005-8. It presents examples of published reactions for the preparation of monofunctional compounds.
The Compendium of Organic Synthetic Methods series facilitates the search for quality, selected functional group transformations, organized by reacting functional group of starting material and functional group formed, with full references to each reaction
Presents examples of published reactions for the preparation of monofunctional compounds from the literature of 2005-8
Provides a handy reference and a valuable tool to the working organic chemist, allowing a quick check of known organic transformations
Stringent criteria for inclusion of reactions, including real synthetic utility of reactions, reagents readily available or easily prepared and handled in the laboratory
Michael B. Smith
Michael B. Smith, University of Connecticut, is a world renowned author of leading organic textbooks.
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Compendium of Organic Synthetic Methods - Michael B. Smith
CHAPTER 1
PREPARATION OF ALKYNES
SECTION 1: ALKYNES FROM ALKYNES
Rahaim, Jr., R.J.; Shaw, J.T. J. Org. Chem. 2008, 73, 2912.
Huang, H.; Liu, H.; Jiang, H.; Chen, K. J. Org. Chem. 2008, 73, 6037.
Moon, J.; Jeong, M.; Nam, H.; Ju, J.; Moon, J.H.; Jung, H-M.; Lee, S. Org. Lett. 2008, 10, 945.
Xie, C.; Liu, L.; Zhang, Y.; Xu, P. Org. Lett. 2008, 10, 2393.
Huang, H.; Jiang, H.; Chen, K.; Liu, H. J. Org. Chem. 2008, 73, 9061.
Monnier, F.; Turtaut, F.; Duroure, L.; Taillefer, M. Org. Lett. 2008, 10, 3203.
Lipshutz, B.H.; Chung, D.W.; Rich, B. Org. Lett. 2008, 10, 3793.
de Lima, P.G.; Antunes, O.A.C. Tetrahedron Lett. 2008, 49, 2506.
Komáromi, A.; Tolnai, G.L.; Novák, Z. Tetrahedron Lett. 2008, 49, 7294.
Uemura, M.; Yorimitsu, H.; Oshima, K. Tetrahedron 2008, 64, 1829.
Mori, S.; Yanase, T.; Aoyagi, S.; Monguchi, Y.; Maegawa, T.; Sajiki, H. Chemistry: European J. 2008, 14, 6994.
Tambade, P.J.; Patil, Y.P.; Nandurkar, N.S.; Bhanage, B.M. Synlett 2008, 886.
de Souza, R.O.M.A.; Bittar, M.S.; Mendes, L.V.P.; da Silva, C.M.F.; da Silva, V.T.; Antunes, O.A.C. Synlett 2008, 1777.
Nishihara, Y.; Inoue, E.; Okada, Y.; Takagi, K. Synlett 2008, 3041.
Brown, W.S.; Boykin, D’A.D.; Sonnier, Jr., M.Q.; Clark, W.D.; Brown, F.V.; Shaughnessy, K.H. Synthesis 2008, 1965.
Zhu, M.; Zhou, Z.; Chen, R. Synthesis 2008, 2680.
Wu, M.; Mao, J.; Guo, J.; Ji, S. Eur. J. Org. Chem. 2008, 4050.
Li, P.; Wang, L.; Wang, M.; You, F. Eur. J. Org. Chem. 2008, 5946.
Tang, B.-X.; Wang, F.; Li, J.-H.; Xie, Y.-X.; Zhang, M.-B. J. Org. Chem. 2007, 72, 6294.
DeRoy, P.L.; Surprenant, S.; Bertrand-Laperle, M.; Yoakim, C. Org. Lett. 2007, 9, 2741.
Guan, J.T.; Weng, T.Q.; Yu, G.-A.; Liu, S.H. Tetrahedron Lett. 2007, 48, 7129.
Cai, M.; Sha, J.; Xu, Q. Tetrahedron 2007, 63, 4642.
Colacino, E.; Daïch, L.; Martinez, J.; Lamaty, F. Synlett 2007, 1279.
Yi, W.-B.; Cai, C.; Wang, X. Eur. J. Org. Chem. 2007, 3445.
Yang, F.; Wu, Y. Eur. J. Org. Chem. 2007, 3476.
Chen, G.; Zhu, X.; Cai, J.; Wan, Y. Synth. Commun. 2007, 37, 1355.
Ren, T.; Zhang, Y.; Zhu, W.; Zhou, J. Synth. Commun. 2007, 37, 3279.
Zhao, Y.; Wang, H.; Hou, X.; Hu, Y.; Lei, A.; Zhang, H; Zhu, L. J. Am. Chem. Soc. 2006, 128, 15048.
Liang, Y.; Xie, Y.-X.; Li, J.-H. J. Org. Chem. 2006, 71, 379.
Yi, C.; Hua, R. J. Org. Chem. 2006, 71, 2535.
Altenhoff, G.; Würtz, S.; Glorius, F. Tetrahedron Lett. 2006, 47, 2925.
Cwik, A.; Hell, Z.; Figueras, F. Tetrahedron Lett. 2006, 47, 3023.
Li, P.; Wang, L. Synlett 2006, 2261.
Hierso, J.C.; Picquet, M.; Cattey, H.; Meunier, P. Synlett 2006, 3005.
Deng, C.-L.; Xie, Y.-X.; Yin, D.-L,; Li, J.-H. Synthesis 2006, 3370.
Torres, G.H.; Choppin, S.; Colobert, F. Eur. J. Org. Chem. 2006, 1450.
Thathagar, M.B.; Rothenberg, G. Org. Biomol. Chem. 2006, 4, 111.
Liang, B.; Dai, M.; Chen, J.; Yang, Z. J. Org. Chem. 2005, 70, 391.
Nakamura, H.; Onagi, S.; Kamakura, T. J. Org. Chem. 2005, 70, 2357.
Jiang, H.; Zhu, S. Tetrahedron Lett. 2005, 46, 517.
Borah, H.N.; Prajapati, D.; Boruah, R.C. Synlett 2005, 2823.
Feuerstein, M.; Doucet, H.; Santelli, M. Tetrahedron Lett. 2005, 46, 1717.
Zhang, G. Synlett 2005, 619.
Li, J.-H.; Zhang, X.-D.; Xie, Y.-X. Synthesis 2005, 804.
Li, J.-H.; Zhang, X.-D.; Xie, Y.-X. Eur. J. Org. Chem. 2005, 4256.
REVIEWS
Alkyne Metathesis
Fürstner, A.; Davies, P.W. Chem. Commun. 2005, 2307.
SECTION 2: ALKYNES FROM ACID DERIVATIVES
Arisawa, M.; Fujimoto, K.; Morinaka, S.; Yamaguchi, M. J. Am. Chem. Soc. 2005, 127, 12226.
SECTION 3: ALKYNES FROM ALCOHOLS AND THIOLS
Sugai, T.; Itoh, A. Tetrahedron Lett. 2007, 48, 9096.
Kabalka, G.W.; Yao, M.-L.; Borella, S. Org. Lett. 2006, 8, 879.
SECTION 4: ALKYNES FROM ALDEHYDES
NO ADDITIONAL EXAMPLES
SECTION 5: ALKYNES FROM ALKYLS, METHYLENES, AND ARYLS
NO ADDITIONAL EXAMPLES
SECTION 6: ALKYNES FROM AMIDES
NO ADDITIONAL EXAMPLES
SECTION 7: ALKYNES FROM AMINES
NO ADDITIONAL EXAMPLES
SECTION 8: ALKYNES FROM ESTERS
Kabalka, G.W.; Naravane, A.; Zhao, L.L. Tetrahedron Lett. 2007, 48, 7091.
SECTION 9: ALKYNES FROM ETHERS, EPOXIDES, AND THIOETHERS
NO ADDITIONAL EXAMPLES
SECTION 10: ALKYNES FROM HALIDES AND SULFONATES
Csékei, M.; Novák, Z.; Kotschy, A. Tetrahedron 2008, 64, 975.
Zhang, W.; Wu, H.; Liu, Z.; Zhong, P.; Zhang, L.; Huang, X.; Cheng, J. Chem. Commun. 2006, 4826.
Qian, M.; Negishi, E.-i. Tetrahedron Lett. 2005, 46, 2927.
SECTION 11: ALKYNES FROM HYDRIDES
Seregin, I.V.; Ryabova, V.; Gevorgyan, V. J. Am. Chem. Soc. 2007, 129, 7742.
For examples of the reaction RC≡CH → RC≡C-C≡CR¹, see Section 300 (Alkyne-Alkyne).
SECTION 12: ALKYNES FROM KETONES
Ghaffarzadeh, M.; Bolourtchian, M.; Fard, Z.H.; Halvagar, M.R.; Mohsenzadeh, F. Synth. Commun. 2006, 36, 1973.
SECTION 13: ALKYNES FROM NITRILES
NO ADDITIONAL EXAMPLES
SECTION 14: ALKYNES FROM ALKENES
Shirakura, M.; Suginome, M. J. Am. Chem. Soc. 2008, 130, 5410.
Chelucci, G.; Capitta, F.; Baldino, S.; Pinn, G.A. Tetrahedron Lett. 2007, 48, 6514.
Okutani, M.; Mori, Y. Tetrahedron Lett. 2007, 48, 6856.
Caporusso, A.M.; Zampieri, A.; Aronica, L.A.; Banti, D. J. Org. Chem. 2006, 71, 1902.
Knöpfel, T.F.; Zarotti, P.; Ichikawa, T.; Carreira, E.M. J. Am. Chem. Soc. 2005, 127, 9682.
SECTION 15: ALKYNES FROM MISCELLANEOUS COMPOUNDS
NO ADDITIONAL EXAMPLES
SECTION 15A: PROTECTION OF ALKYNES
Orsini, A.; Vitérisi, A.; Bodlenner, A.; Weibel, J.-M.; Pale, P. Tetrahedron Lett. 2005, 46, 259.
CHAPTER 2
PREPARATION OF ACID DERIVATIVES
SECTION 16: ACID DERIVATIVES FROM ALKYNES
NO ADDITIONAL EXAMPLES
SECTION 17: ACID DERIVATIVES FROM ACID DERIVATIVES
Serieys, A.; Botuha, C.; Chemla, F.; Ferreira, F.; Pérez-Luna, A. Tetrahedron Lett. 2008, 49, 5322.
SECTION 18: ACID DERIVATIVES FROM ALCOHOLS AND THIOLS
Hirano, J.-i.; Miyamoto, K.; Ohta, H. Tetrahedron Lett. 2008, 49, 1217.
Mannam, S.; Sekar, G. Tetrahedron Lett. 2008, 49, 2457.
Ballistreri, F.P.; Tomaselli, G.A.; Toscano, R.M. Tetrahedron Lett. 2008, 49, 3291.
Grill, J.M.; Ogle, J.W.; Miller, S.A. J. Org. Chem. 2006, 71, 9291.
Svetlakov, N.V.; Nikitin, V.G.; Nikolaeva, E.A. Russ. J. Org. Chem. 2007, 43, 773.
Hirashima, S.-i.; Hashimoto, S.; Masaki, Y.; Itoh, A. Tetrahedron 2006, 62, 7887.
Kuwabara, K.; Itoh, A. Synthesis 2006, 1949.
Wang, J.; Yan, L.; Li, G.; Wang, X.; Ding, Y.; Suo, J. Tetrahedron Lett. 2005, 46, 7023.
SECTION 19: ACID DERIVATIVES FROM ALDEHYDES
Cafiero, L.R.; Snowden, T.S. Org. Lett. 2008, 10, 3853.
Lim, M.; Yoon, C.-M.; An, G.; Rhee, H. Tetrahedron Lett. 2007, 48, 3835.
Hashemi, M.M.; Ghazanfari, D.; Ahmadibeni, Y.; Karimi-Jaberi, Z.; Ezabadi, A. Synth. Commun. 2005, 35, 1103.
SECTION 20: ACID DERIVATIVES FROM ALKYLS, METHYLENES, AND ARYLS
Sugai, T.; Itoh, A. Tetrahedron Lett. 2007, 48, 2931.
Hirashima, S.-i.; Itoh, A. Synthesis 2006, 1757.
Gupta, M.; Paul, S.; Gupta, R.; Loupy, A. Tetrahedron Lett. 2005, 46, 495.
SECTION 21: ACID DERIVATIVES FROM AMIDES
NO ADDITIONAL EXAMPLES
SECTION 22: ACID DERIVATIVES FROM AMINES
Naik, R.; Pasha, M.A. Synth. Commun. 2006, 36, 165.
SECTION 23: ACID DERIVATIVES FROM ESTERS
Fotakopoulou, I.; Barbayianni, E.; Constantinou-Kokotou, V.; Bornscheuer, U.T.; Kokotos, G. J. Org. Chem. 2007, 72, 782.
Goel, A.; Verma, D.; Dixit, M.; Raghunandan, R.; Maulik, P.R. J. Org. Chem. 2006, 71, 804.
Lesma, G.; Sacchetti, A.; Silvani, A. Synthesis 2006, 594.
Nishiguchi, A.; Maeda, K.; Miki, S. Synthesis 2006, 4131.
Barbayianni, E.; Fotakopoulou, I.; Schmidt, M.; Constantinou-Kokotou, V.; Bornscheuer, U.T.; Kokotos, G. J. Org. Chem. 2005, 70, 8730.
Other reactions useful for the hydrolysis of esters may be found in Section 30A (Protection of Carboxylic Acid Derivatives).
SECTION 24: ACID DERIVATIVES FROM ETHERS, EPOXIDES, AND THIOETHERS
Rowley, J.M.; Lobkovsky, E.B.; Coates, G.W. J. Am. Chem. Soc. 2007, 129, 4948.
Svetlakov, N.V.; Nikitin, V.G.; Nikolaeva, E.A. Russ. J. Org. Chem. 2007, 43, 771.
SECTION 25: ACID DERIVATIVES FROM HALIDES AND SULFONATES
Niu, D.-F.; Xiao, L.-P.; Zhang, A.-J.; Zhang, G.-R.; Tan, Q.-Y.; Lu, J.-X. Tetrahedron 2008, 64, 10517.
Cacchi, S.; Cotet, C.L.; Fabrizi, G.; Forte, G.; Goggiamani, A.; Martín, L.; Martínez, S.; Molins, E.; Moreno-Mañas, M.; Petrucci, F.; Roig, A.; Vallribera, A. Tetrahedron 2007, 63, 2519.
Zhao, X.; Alper, H.; Yu, Z. J. Org. Chem. 2006, 71, 3988.
Berger, P.; Bessmernykh, A.; Caille, J.-C.; Mignonac, S. Synthesis 2006, 3106.
Nadal, M.L.; Bosch, J.; Vila, J.M.; Klein, G.; Ricart, S.; Moretó, J.S. J. Am. Chem. Soc. 2005, 127, 10476.
Jones, R.V.H.; Lindsell, W.E.; Palmer, D.D.; Preston, P.N.; Whitton, A.J. Tetrahedron Lett. 2005, 46, 8695.
Mutule, I.; Suna, E. Tetrahedron 2005, 61, 11168.
SECTION 26: ACID DERIVATIVES FROM HYDRIDES
Giri, R.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 14082.
Crich, D.; Zou, Y. J. Org. Chem. 2005, 70, 3309.
Ohashi, S.; Sakaguchi, S.; Ishii, Y. Chem. Commun. 2005, 486.
SECTION 27: ACID DERIVATIVES FROM KETONES
Zhang, Y.; Jiao, J.; Flowers, II, R.A. J. Org. Chem. 2006, 71, 4516.
SECTION 28: ACID DERIVATIVES FROM NITRILES
Mukherjee, C.; Zhu, D.; Biehl, E.R.; Parmar, R.R.; Hua, L. Tetrahedron 2006, 62, 6150.
SECTION 29: ACID DERIVATIVES FROM ALKENES
Williams, C.M.; Johnson, J.B.; Rovis, T. J. Am. Chem. Soc. 2008, 130, 14936.
Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2008, 130, 15254.
Tanaka, R.; Nakano, K.; Nozaki, K. J. Org. Chem. 2007, 72, 8671.
SECTION 30: ACID DERIVATIVES FROM MISCELLANEOUS COMPOUNDS
Yeung, C.S.; Dong, V.M. J. Am. Chem. Soc. 2008, 130, 7826.
Ochiai, H.; Jang, M.; Hirano, K.; Yorimitsu, H.; Oshima, K. Org. Lett. 2008, 10, 2681.
Takaya, J.; Tadami, S.; Ukai, K.; Iwasawa, N. Org. Lett. 2008, 10, 2697.
Khurana, J.M.; Sharma, P.; Gogia, A.; Kandpal, B.M. Org. Prep. Proceed. Int. 2007, 39, 185.
Ukai, K.; Aoki, M.; Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2006, 128, 8706.
SECTION 30A: PROTECTION OF CARBOXYLIC ACID DERIVATIVES
NO ADDITIONAL EXAMPLES
Other reactions useful for the protection of carboxylic acids are included in Section 107 (Esters from Carboxylic Acid Derivatives) and Section 23 (Carboxylic Acid Derivatives from Esters).
Taksande, K.N.; Sakate, S.S.; Lokhande, P.D. Tetrahedron Lett. 2006, 47, 643.
CHAPTER 3
PREPARATION OF ALCOHOLS
SECTION 31: ALCOHOLS AND THIOLS FROM ALKYNES
NO ADDITIONAL EXAMPLES
SECTION 32: ALCOHOLS AND THIOLS FROM ACID DERIVATIVES
Zhou, Y.; Gao, G.; Li, H.; Qu, J. Tetrahedron Lett. 2008, 49, 3260.
Wei, Y.-J.; Ren, H.; Wang, J.-X. Tetrahedron Lett. 2008, 49, 5697.
Ohta, T.; Kamiya, M.; Nobutomo, M.; Kusui, K.; Furukawa, I. Bull. Chem. Soc. Jpn. 2005, 78, 1856.
SECTION 33: ALCOHOLS AND THIOLS FROM ALCOHOL AND THIOLS
Kim, I.S.; Ngai, M.-Y.; Krische, M.J. J. Am. Chem. Soc. 2008, 130, 6340.
Fujita, K.-i.; Asai, C.; Yamaguchi, T.; Hanasaka, F.; Yamaguchi, R. Org. Lett. 2005, 7, 4017.
SECTION 34: ALCOHOLS AND THIOLS FROM ALDEHYDES
The following reaction types are included in this section:
A. Reductions of Aldehydes to Alcohols
B. Alkylation of Aldehydes, Forming Alcohols
SECTION 34A: REDUCTIONS OF ALDEHYDES TO ALCOHOLS
Su, F.-Z.; He, L.; Ni, J.; Cao, Y.; He, H.-Y.; Fan, K.-N. Chem. Commun. 2008, 3531.
Sambher, S.; Baskar, C.; Dhillon, R.S. Synth. Commun. 2008, 38, 2150.
Xie, J.-H.; Zhou, Z.-T.; Kong, W.-L.; Zhou, Q.-L. J. Am. Chem. Soc. 2007, 129, 1868.
Casey, C.P.; Guan, H. J. Am. Chem. Soc. 2007, 129, 5816.
Shaikh, N.S.; Junge, K.; Beller, M. Org. Lett. 2007, 9, 5429.
Heydari, A.; Khaksar, S.; Akbari, J.; Esfandyari, M.; Pourayoubi, M.; Tajbakhsh, M. Tetrahedron Lett. 2007, 48, 1135.
Omote, M.; Tanaka, N.; Tarui, A.; Sato, K.; Kumadaki, I.; Ando, A. Tetrahedron Lett. 2007, 48, 2989.
Wessjohann, L.A.; Schrekker, H.S. Tetrahedron Lett. 2007, 48, 4323.
Li, X.; List, B. Chem. Commun. 2007, 1739.
Giacomini, D.; Galletti, P.; Quintavalla, A.; Gucciardo, G.; Paradisi, F. Chem. Commun. 2007, 4038.
Kidwai, M.; Bansal, V.; Saxena, A.; Shankar, R.; Mozumdar, S. Tetrahedron Lett. 2006, 47, 4161.
Xing, Y.; Chen, J.-S.; Dong, Z.-R.; Li, Y.-Y.; Gao, J.-X. Tetrahedron Lett. 2006, 47, 4501.
REVIEW
Transition Metal-Catalyzed Hydrosilylation Of Carbonyl Compounds And Imines. A Review
Díez-González, S.; Nolan, S.P. Org. Prep. Proceed. Int. 2007, 39, 523.
SECTION 34B: ALKYLATION OF ALDEHYDES, FORMING ALCOHOLS
ASYMMETRIC ALKYLATIONS
Kim, H.; MacMillan, D.W.C. J. Am. Chem. Soc. 2008, 130, 398.
Boxer, M.B.; Akakura, M.; Yamamoto, H. J. Am. Chem. Soc. 2008, 130, 1580.
Hajra, S.; Giri, A.K. J. Org. Chem. 2008, 73, 3935.
Jin, M.-J.; Sarkar, S.M.; Lee, D.-H.; Qiu, H. Org. Lett. 2008, 10, 1235.
Appelt, H.R.; Limberger, J.B.; Weber, M.; Rodrigues, O.E.D.; Oliveira, J.S.; Lüdtke, D.S.; Braga, A.L. Tetrahedron Lett. 2008, 49, 4956.
Huang, X.; Wu, L.; Xu, J.; Zong, L.; Hu, H.; Cheng, Y. Tetrahedron Lett. 2008, 49, 6823.
Burguete, M.I.; Escorihuela, J.; Luis, S.V.; Lledós, A.; Ujaque, G. Tetrahedron 2008, 64, 9717.
Malkov, A.V.; Westwater, M.-M.; Gutnov, A.; Ramírez-López, P.; Friscourt, F.; Kadlčíková, A.; Hodačová, J.; Rankovic, Z.; Kotora, M.; Kočovský, P. Tetrahedron 2008, 64, 11335.
Parrott II, R.W.; Dore, D.D.; Chandrashekar, S.P.; Bentley, J.T.; Morgan, B.S.; Hitchcock, S.R. Tetrahedron Asymmetry 2008, 19, 607.
Cheng, Y.-Q.; Bian, Z.; Kang, C.-Q.; Guo, H.-Q.; Gao, L.-X. Tetrahedron Asymmetry 2008, 19, 1572.
Grach, G.; Reboul, V.; Metzner, P. Tetrahedron Asymmetry 2008 19, 1744.
Muramatsu, Y.; Harada, T. Angew. Chem. Int. Ed. 2008, 47, 1088.
Tanaka, T.; Sano, Y.; Hayashi, M. Chemistry: Asian J. 2008, 3, 1465.
Simonini, V.; Benaglia, M.; Pignataro, L.; Guizzetti, S.; Celentano, G. Synlett 2008, 1061.
Hrdina, R.; Boyd, T.; Valterová, I.; Hodačová, J.; Kotora, M. Synlett 2008, 3141.
Yamamoto, K.; Tsurumi, K.; Sakurai, F.; Kondo, K.; Aoyama, T. Synthesis 2008, 3585.
Ukon, T.; Harada, T. Eur. J. Org. Chem. 2008, 4405.
Hargaden, G.C.; O’Sullivan, T.P.; Guiry, P.J. Org. Biomol. Chem. 2008, 6, 562.
Ramasastry, S.S.V.; Zhang, H.; Tanaka, F.; Barbas, III, C.F. J. Am. Chem. Soc. 2007, 129, 288.
Yang, Y.; Zhu, S.-F.; Duan, H.-F.; Zhou, C.-Y.; Wang, L.-X.; Zhou, Q.-L. J. Am. Chem. Soc. 2007, 129, 2248.
Lee, S.; MacMillan, D.W.C. J. Am. Chem. Soc. 2007, 129, 15438.
Huang, Z.; Lai, H.; Qin, Y. J. Org. Chem. 2007, 72, 1373.
Milburn, R.R.; Shakil Hussain, S.M.; Prien, O.; Ahmed, Z.; Snieckus, V. Org. Lett. 2007, 9, 4403.
Sedelmeier, J.; Bolm, C. J. Org. Chem. 2007, 72, 8859.
Cortez, N.A.; Aguirre, G.; Parra-Hake, M.; Somanathan, R. Tetrahedron Lett. 2007, 48, 4335.
Takeuchi, K.; Takeda, T.; Fujimoto, T.; Yamamoto, I. Tetrahedron 2007, 63, 5319.
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