Catalytic asymmetric synthesis of chiral allylic esters

Journal of the American Chemical Society

Volumn 127, Issue 9, 2005, Pages 2866-2867

  Kirsch, Stefan F ^a,b   Overman, Larry E ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; ESTER;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHIRALITY; ENANTIOSELECTIVITY; ESTERIFICATION; PREDICTION; ROOM TEMPERATURE;

ALLYL COMPOUNDS; CATALYSIS; ESTERS; PALLADIUM; STEREOISOMERISM; TRICHLOROACETIC ACID;

EID: 14844297329     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0425583     Document Type: Article

References (39)

1. Using enzymes: for reviews, see: (a) Carrea, G.; Riva, S. Angew. Chem., Int. Ed. 2000, 39, 2226-2254. (b) Enzyme Catalysis in Organic Synthesis: Drauz, K., Waldmann, H., Eds.; VCH: Weinheim, Germany, 1995. Illustrative examples: (c) Enders, D.; Nguyen, D. Synthesis 2000, 2092-2098. (d) Itoh, T.; Sakabe, K.; Kudo, K.; Zagatti, P.; Renou, M. Tetrahedron Lett. 1998, 39, 4071-4074. (e) Takagi, Y.; Teramoto, J.; Kihara, H.; Itoh, T.; Tsukube, H. Tetrahedron Lett. 1996, 37, 4991-4992. (f) Takahata, H.; Uchida, Y.; Momose, T. Tetrahedron Lett. 1992, 33, 3331-3332. This procedure is optimal when coupled with in situ racemization; for a recent example and leading references, see: (g) Choi, J. H.; Choi, Y. K.; Kim, Y. K.; Park, E. S.; Kim, E. J.; Kim, M.-J.; Park, J. J. Org. Chem. 2004, 69, 1972-1977.
2. Using enzymes: for reviews, see: (a) Carrea, G.; Riva, S. Angew. Chem., Int. Ed. 2000, 39, 2226-2254. (b) Enzyme Catalysis in Organic Synthesis: Drauz, K., Waldmann, H., Eds.; VCH: Weinheim, Germany, 1995. Illustrative examples: (c) Enders, D.; Nguyen, D. Synthesis 2000, 2092-2098. (d) Itoh, T.; Sakabe, K.; Kudo, K.; Zagatti, P.; Renou, M. Tetrahedron Lett. 1998, 39, 4071-4074. (e) Takagi, Y.; Teramoto, J.; Kihara, H.; Itoh, T.; Tsukube, H. Tetrahedron Lett. 1996, 37, 4991-4992. (f) Takahata, H.; Uchida, Y.; Momose, T. Tetrahedron Lett. 1992, 33, 3331-3332. This procedure is optimal when coupled with in situ racemization; for a recent example and leading references, see: (g) Choi, J. H.; Choi, Y. K.; Kim, Y. K.; Park, E. S.; Kim, E. J.; Kim, M.-J.; Park, J. J. Org. Chem. 2004, 69, 1972-1977.
3. Using enzymes: for reviews, see: (a) Carrea, G.; Riva, S. Angew. Chem., Int. Ed. 2000, 39, 2226-2254. (b) Enzyme Catalysis in Organic Synthesis: Drauz, K., Waldmann, H., Eds.; VCH: Weinheim, Germany, 1995. Illustrative examples: (c) Enders, D.; Nguyen, D. Synthesis 2000, 2092-2098. (d) Itoh, T.; Sakabe, K.; Kudo, K.; Zagatti, P.; Renou, M. Tetrahedron Lett. 1998, 39, 4071-4074. (e) Takagi, Y.; Teramoto, J.; Kihara, H.; Itoh, T.; Tsukube, H. Tetrahedron Lett. 1996, 37, 4991-4992. (f) Takahata, H.; Uchida, Y.; Momose, T. Tetrahedron Lett. 1992, 33, 3331-3332. This procedure is optimal when coupled with in situ racemization; for a recent example and leading references, see: (g) Choi, J. H.; Choi, Y. K.; Kim, Y. K.; Park, E. S.; Kim, E. J.; Kim, M.-J.; Park, J. J. Org. Chem. 2004, 69, 1972-1977.
4. Using enzymes: for reviews, see: (a) Carrea, G.; Riva, S. Angew. Chem., Int. Ed. 2000, 39, 2226-2254. (b) Enzyme Catalysis in Organic Synthesis: Drauz, K., Waldmann, H., Eds.; VCH: Weinheim, Germany, 1995. Illustrative examples: (c) Enders, D.; Nguyen, D. Synthesis 2000, 2092-2098. (d) Itoh, T.; Sakabe, K.; Kudo, K.; Zagatti, P.; Renou, M. Tetrahedron Lett. 1998, 39, 4071-4074. (e) Takagi, Y.; Teramoto, J.; Kihara, H.; Itoh, T.; Tsukube, H. Tetrahedron Lett. 1996, 37, 4991-4992. (f) Takahata, H.; Uchida, Y.; Momose, T. Tetrahedron Lett. 1992, 33, 3331-3332. This procedure is optimal when coupled with in situ racemization; for a recent example and leading references, see: (g) Choi, J. H.; Choi, Y. K.; Kim, Y. K.; Park, E. S.; Kim, E. J.; Kim, M.-J.; Park, J. J. Org. Chem. 2004, 69, 1972-1977.
5. Using enzymes: for reviews, see: (a) Carrea, G.; Riva, S. Angew. Chem., Int. Ed. 2000, 39, 2226-2254. (b) Enzyme Catalysis in Organic Synthesis: Drauz, K., Waldmann, H., Eds.; VCH: Weinheim, Germany, 1995. Illustrative examples: (c) Enders, D.; Nguyen, D. Synthesis 2000, 2092-2098. (d) Itoh, T.; Sakabe, K.; Kudo, K.; Zagatti, P.; Renou, M. Tetrahedron Lett. 1998, 39, 4071-4074. (e) Takagi, Y.; Teramoto, J.; Kihara, H.; Itoh, T.; Tsukube, H. Tetrahedron Lett. 1996, 37, 4991-4992. (f) Takahata, H.; Uchida, Y.; Momose, T. Tetrahedron Lett. 1992, 33, 3331-3332. This procedure is optimal when coupled with in situ racemization; for a recent example and leading references, see: (g) Choi, J. H.; Choi, Y. K.; Kim, Y. K.; Park, E. S.; Kim, E. J.; Kim, M.-J.; Park, J. J. Org. Chem. 2004, 69, 1972-1977.
6. Using enzymes: for reviews, see: (a) Carrea, G.; Riva, S. Angew. Chem., Int. Ed. 2000, 39, 2226-2254. (b) Enzyme Catalysis in Organic Synthesis: Drauz, K., Waldmann, H., Eds.; VCH: Weinheim, Germany, 1995. Illustrative examples: (c) Enders, D.; Nguyen, D. Synthesis 2000, 2092-2098. (d) Itoh, T.; Sakabe, K.; Kudo, K.; Zagatti, P.; Renou, M. Tetrahedron Lett. 1998, 39, 4071-4074. (e) Takagi, Y.; Teramoto, J.; Kihara, H.; Itoh, T.; Tsukube, H. Tetrahedron Lett. 1996, 37, 4991-4992. (f) Takahata, H.; Uchida, Y.; Momose, T. Tetrahedron Lett. 1992, 33, 3331-3332. This procedure is optimal when coupled with in situ racemization; for a recent example and leading references, see: (g) Choi, J. H.; Choi, Y. K.; Kim, Y. K.; Park, E. S.; Kim, E. J.; Kim, M.-J.; Park, J. J. Org. Chem. 2004, 69, 1972-1977.
7. Using enzymes: for reviews, see: (a) Carrea, G.; Riva, S. Angew. Chem., Int. Ed. 2000, 39, 2226-2254. (b) Enzyme Catalysis in Organic Synthesis: Drauz, K., Waldmann, H., Eds.; VCH: Weinheim, Germany, 1995. Illustrative examples: (c) Enders, D.; Nguyen, D. Synthesis 2000, 2092-2098. (d) Itoh, T.; Sakabe, K.; Kudo, K.; Zagatti, P.; Renou, M. Tetrahedron Lett. 1998, 39, 4071-4074. (e) Takagi, Y.; Teramoto, J.; Kihara, H.; Itoh, T.; Tsukube, H. Tetrahedron Lett. 1996, 37, 4991-4992. (f) Takahata, H.; Uchida, Y.; Momose, T. Tetrahedron Lett. 1992, 33, 3331-3332. This procedure is optimal when coupled with in situ racemization; for a recent example and leading references, see: (g) Choi, J. H.; Choi, Y. K.; Kim, Y. K.; Park, E. S.; Kim, E. J.; Kim, M.-J.; Park, J. J. Org. Chem. 2004, 69, 1972-1977.
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9. Using chemical catalysts, see inter alia: (a) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; Chapter 6A. (b) Fischer, C.; Defieber, C.; Suzuki, T.; Carreira, E. M. J. Am. Chem. Soc. 2004, 126, 1628-1629. (c) Martín, V. S.; Ode, J. M.; Palazón, J. M.; Soler, M. A. Tetrahedron: Asymmetry 1992, 3, 573-580.
10. Using chemical catalysts, see inter alia: (a) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; Chapter 6A. (b) Fischer, C.; Defieber, C.; Suzuki, T.; Carreira, E. M. J. Am. Chem. Soc. 2004, 126, 1628-1629. (c) Martín, V. S.; Ode, J. M.; Palazón, J. M.; Soler, M. A. Tetrahedron: Asymmetry 1992, 3, 573-580.
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12. For other representative methods, see: (a) Boyall, D.; Lopez, F.; Sasaki, H.; Frantz, D.; Carreira, E. M. Org. Lett. 2000, 2, 4233-4236. (b) Corey, E. J.; Guzman-Perez, A.; Lazerwith, S. E. J. Am. Chem. Soc. 1997, 119, 11769-11776. (c) RajanBabu, T. V.; Nugent, W. A. J. Am. Chem. Soc. 1994, 116, 986-997. (d) Busche-Hünnefeld, J. L.; Seebach, D. Tetrahedron 1992, 48, 5719-5730. (e) Oppolzer, W.; Radinov, R. N. Tetrahedron Lett. 1988, 29, 5645-5648.
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37. 1.
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