Practical enantioselective diels-alder and aldol reactions using a new chiral controller system

Journal of the American Chemical Society

Volumn 111, Issue 14, 1989, Pages 5493-5495

  Corey, E J ^a   Imwinkelried, René ^a   Pikul, Stanislaw ^a   Xiang, Yi Bin ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845185615     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00196a081     Document Type: Article

References (8)

1. For recent references on enantioselective Diels-Alder reactions, see: (a) Helmchen, G.; Karge, R.; Weetman, J. In Modern Synthetic Methods; Scheffold, R., Ed.; Springer Verlag: Berlin, 1986; Vol, 4, p 261; (b) Nachr. Chem. Tech. Lab. 1987, 35, 836. (c) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1984, 23, 876. (d) Yamamoto, H.; Maruoka, K.; Furuta, K.; Ikeda, N.; Mori, A. In Stereochemistry of Organic and Bioorganic Transformations; Bartmann, W., Sharpless, K. B., Eds.; VCH Publishers: Weinheim, 1987; p 13. (e) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310. (f) Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238. (g) Narasaka, K.; Inoue, M.; Okada, N. Chem. Lett. 1986, 1109. (h) Chapuis, C.; Jurczak, J. Helv. Chim. Acta 1987, 70, 436. (i) Furata, K.; Miwa, Y.; Iwanaga, K.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 6254.
2. For references on enantioselective aldol methodology, see: (a) Evans, D. A. Aldrich. Acta 1982, 15, 23. (b) Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127. (c) Evans, D. A.; Sjogren, E. B.; Weber, A. E.; Conn, R. E. Tetrahedron Lett. 1987, 28, 39. (d) Masamune, S.; Sato, T.; Kim, B. M.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279. (e) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405. (f) Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1985, 26, 5807. (g) Brown, M.; Devant, R. Tetrahedron Lett. 1984, 25, 5031. (h) Ambler, P. W.; Davies, S. G. Tetrahedron Lett. 1985, 26, 2129. (i) Patterson, I. Chem. Ind. (London) 1988, 390.
3. Williams, O. F.; Bailar, J. C. J. Am. Chem. Soc. 1959, 81, 4464. See, also: Saigo, K.; Kubota, N.; Takebayashi, S.; Hasegawa, M. Bull. Chem. Soc. Jpn. 1986, 59, 931.
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5. Corey, E. J.; Ensley, H. E. J. Am. Chem. Soc. 1975, 97, 6908. (b) Corey, E. J.; Cheng, X.-M. The Logic of Chemical Synthesis; John Wiley: New York, 1989; pp 255–264.
6. Farmer, R. F.; Hamer, J. J. Org. Chem. 1966, 31, 2418.
7. Schmuff, N. R.; Phillips, J. K.; Burkholder, W. E.; Fales, H. M.; Chen, C.-W.; Roller, P. P.; Ma, M. Tetrahedron Lett. 1984, 25, 1533.
8. For literature, see: (a) Hirama, M.; Garvey, D. S.; Lu, L. D. L.; Masamune, S. Tetrahedron Lett. 1979, 3937. (b) Heathcock, C. H.; White, C. T.; Morrison. J. J.; Van Derveer, D. J. Org. Chem. 1981, 46, 1296. (c) Masamune, S.; Choy, W.; Kerdesky, F. A. J.; Imperiali, B. J. Am. Chem. Soc. 1981, 103, 1566. References 11a and 1 lb refer to the free β-hydroxy acids which were obtained as indicated in ref 10.