Asymmetric construction of quaternary carbon centers by regio- and enantiocontrolled allylzincation

Organic Letters

Volumn 2, Issue 15, 2000, Pages 2193-2196

  Nakamura, Masaharu ^a   Inoue, Toshihiro ^a   Sato, Akihito ^a   Nakamura, Eiichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000659278     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005892m     Document Type: Article

References (31)

1. For reviews, see: (a) Martin, S. F. Tetrahedron 1980, 36, 419-460.
2. (b) Fuji, K. Chem Rev. 1993, 93, 2037-2066
3. (c) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 389-401.
4. For reviews, see: (a) Rossiter, B. E. Swingle, N. M. Chem. Rev. 1992, 92, 771-806.
5. Organozinc addition: (b) Soai, K.; Shibata, T. In Organozinc Reagents. A Practical Approach; Knochel, P., Jones, P., Eds.; Oxford University Press: New York, 1999; Chapter 12.5.
6. (a) Nakamura, M.; Hirai, A.; Sogi, M.; Nakamura, E. J. Am. Chem. Soc. 1998, 120, 5846-5847.
7. (b) Nakamura, M.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 1996, 118, 8489-8490.
8. (c) Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 52, 8997-9000.
9. (a) Nakamura, M.; Arai, M.; Nakamura, E. J. Am. Chem. Soc. 1995, 117, 1179-1180.
10. (b) Nakamura, M.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 2000, 122, 978-979
11. Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1990, 112, 7428-7430.
12. Such substituted cyclopropenone acetals are readily available from 1,3-dichloroacetone on a large scale. Isaka, M.; Ejiri, S.; Nakamura, E. Tetrahedron 1992, 48, 2045-2057.
13. Nakamura, E.; Miyachi, Y.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1992, 114, 6686-6692. See also: Hirai, A.; Nakamura, M.; Nakamura, E. J. Am. Chem. Soc. 1999, 121, 8665-8666 and references cited therein.
14. Nakamura, E.; Miyachi, Y.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1992, 114, 6686-6692. See also: Hirai, A.; Nakamura, M.; Nakamura, E. J. Am. Chem. Soc. 1999, 121, 8665-8666 and references cited therein.
15. Nakamura, M.; Nakamura, E. Computational Studies on Diastereo- and Enantioselectivities of Allylmetalation of Cyclopropenone Acetals. In Electronic Conference Heterocyclic Chemistry; Rzepa, H. S., Snyder, J., Leach, C., Eds.; Royal Society of Chemistry: London, 1997; ISBN 0-85404-894-4. See also: Kubota, K.; Mori, S.; Nakamura, M.; Nakamura, E. J. Am. Chem. Soc. 1998, 120, 13334-13341.
16. Nakamura, M.; Nakamura, E. Computational Studies on Diastereo- and Enantioselectivities of Allylmetalation of Cyclopropenone Acetals. In Electronic Conference Heterocyclic Chemistry; Rzepa, H. S., Snyder, J., Leach, C., Eds.; Royal Society of Chemistry: London, 1997; ISBN 0-85404-894-4. See also: Kubota, K.; Mori, S.; Nakamura, M.; Nakamura, E. J. Am. Chem. Soc. 1998, 120, 13334-13341.
17. 2: C, 79.03; H, 8.59. Found: C, 79.07; H, 8.83. The R-configuration of this product was determined through an eight-step conversion to (R)-2-methyl-2-phenylbutanoic acid.
18. (a) le Noble, W. J.; Kelm, H. Angew. Chem., Int. Ed. Engl. 1980, 19, 841 -946.
19. (b) Matsumoto, K.; Sera, A.; Uchida, T. Synthesis 1985, 1-26.
20. (c) Matsumoto, K.; Sera, A. Synthesis 1985, 999-1027.
21. (d) van Eldik, R.; Asano, T.; le Noble, W. J. Chem. Rev. 1989, 89, 549-688.
22. (e) Isaccs, N. S. Tetrahedron 1991, 47, 8463-8497.
23. Kubota, K.; Isaka, M.; Nakamura, M.; Nakamura, E. J. Am. Chem. Soc. 1993, 115, 5867-5868.
24. (a) Buell, G. R.; Corriu, R.; Christian, G.; Spialter, L. J. Am. Chem. Soc. 1970, 92, 7424-7428.
25. (b) Cason, L. F.; Brooks, H. G. J. Org. Chem. 1954 19, 1278-1282.
26. (c) Seyferth, D.; Wada, T. Inorg. Chem. 1962, 1, 78-83. Stober, M. R.; Michael, K. W.; Speier, J. L. J. Org. Chem. 1967, 32, 2740-2744.
27. (c) Seyferth, D.; Wada, T. Inorg. Chem. 1962, 1, 78-83. Stober, M. R.; Michael, K. W.; Speier, J. L. J. Org. Chem. 1967, 32, 2740-2744.
28. Asymmetric synthesis: (d) Tamao, K.; Kanatani, R.; Kumada, H. Tetrahedron Lett. 1984, 25, 1913-1916.
29. Nakamura, E.; Kubota, K. Tetrahedron Lett. 1997, 38, 7099-7102.
30. Nakamura, M.; Hara, K.; Sakata, G.; Nakamura. E. Org. Lett. 1999, 1, 1505-1507.
31. 1H NMR coupling analysis and is in accord with the syn-addition mode of the carbometalation (ref 5).