1,5-Asymmetric Induction in Methyl Ketone Aldol Addition Reactions

Journal of Organic Chemistry

Volumn 62, Issue 4, 1997, Pages 788-789

  Evans, David A ^a   Coleman, Paul J ^a   Côté, Bernard ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000271703     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962417m     Document Type: Article

References (26)

1. For general approaches to the synthesis of 1,3-diol relationships in conjunction with C-C bond formation see: (a) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753-1765. (b) Mora, Y.; Asai, M.; Okumura, A.; Furukawa, H. Tetrahedron 1995, 51, 5299-5314. Knochel, P.; Brieden, W.; Rozema, M. J.; Eisenberg, C. Tetrahedron Lett. 1993, 34, 5881-5884.
2. For general approaches to the synthesis of 1,3-diol relationships in conjunction with C-C bond formation see: (a) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753-1765. (b) Mora, Y.; Asai, M.; Okumura, A.; Furukawa, H. Tetrahedron 1995, 51, 5299-5314. Knochel, P.; Brieden, W.; Rozema, M. J.; Eisenberg, C. Tetrahedron Lett. 1993, 34, 5881-5884.
3. For general approaches to the synthesis of 1,3-diol relationships in conjunction with C-C bond formation see: (a) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753-1765. (b) Mora, Y.; Asai, M.; Okumura, A.; Furukawa, H. Tetrahedron 1995, 51, 5299-5314. Knochel, P.; Brieden, W.; Rozema, M. J.; Eisenberg, C. Tetrahedron Lett. 1993, 34, 5881-5884.
4. (a) Evans, D. A.; Duffy, J. L.; Dart, M. J. Tetrahedron Lett. 1994, 35, 8537-8540.
5. (b) Evans, D. A.; Dart, M. J.; Duffy, J. L.; Yang, M. G. J. Am. Chem. Soc., 1996, 118, 4322-4343.
6. (a) Blanchette, M. A.; Malamas, M. S.; Nantz, M. H.; Roberts, J. C.; Somfai, P.; Whritenour, D. C.; Masamune, S. J. Org. Chem. 1989, 54, 2817-2825.
7. (b) Seebach, D.; Misslitz, U.; Uhlmann, P. Angew. Chem., Int. Ed. Engl. 1989, 28, 472-473.
8. For 1,4-induction in acetate aldol reactions see: (a) Zibuck, R.; Liverton, N. J.; Smith, A. B. J. Am. Chem. Soc. 1986, 108, 2451-2453. (b) Braun, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 24-37. Paterson, I.; Goodman, J. M.; Isaka, M. Tetrahedreon Lett. 1989, 30, 7121-7124. Trost, B. M.; Urabe, H. J. Org. Chem. 1990, 55, 3982-3983. (e) Roush, W. R.; Bannister, T. D. Tetrahedron Lett. 1992, 33, 3587-3590. (f) Lagu, B. R.; Liotta, D. C. Tetrahedron Lett. 1994, 35, 4485-4488.
9. For 1,4-induction in acetate aldol reactions see: (a) Zibuck, R.; Liverton, N. J.; Smith, A. B. J. Am. Chem. Soc. 1986, 108, 2451-2453. (b) Braun, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 24-37. Paterson, I.; Goodman, J. M.; Isaka, M. Tetrahedreon Lett. 1989, 30, 7121-7124. Trost, B. M.; Urabe, H. J. Org. Chem. 1990, 55, 3982-3983. (e) Roush, W. R.; Bannister, T. D. Tetrahedron Lett. 1992, 33, 3587-3590. (f) Lagu, B. R.; Liotta, D. C. Tetrahedron Lett. 1994, 35, 4485-4488.
10. For 1,4-induction in acetate aldol reactions see: (a) Zibuck, R.; Liverton, N. J.; Smith, A. B. J. Am. Chem. Soc. 1986, 108, 2451-2453. (b) Braun, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 24-37. Paterson, I.; Goodman, J. M.; Isaka, M. Tetrahedreon Lett. 1989, 30, 7121-7124. Trost, B. M.; Urabe, H. J. Org. Chem. 1990, 55, 3982-3983. (e) Roush, W. R.; Bannister, T. D. Tetrahedron Lett. 1992, 33, 3587-3590. (f) Lagu, B. R.; Liotta, D. C. Tetrahedron Lett. 1994, 35, 4485-4488.
11. For 1,4-induction in acetate aldol reactions see: (a) Zibuck, R.; Liverton, N. J.; Smith, A. B. J. Am. Chem. Soc. 1986, 108, 2451-2453. (b) Braun, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 24-37. Paterson, I.; Goodman, J. M.; Isaka, M. Tetrahedreon Lett. 1989, 30, 7121-7124. Trost, B. M.; Urabe, H. J. Org. Chem. 1990, 55, 3982-3983. (e) Roush, W. R.; Bannister, T. D. Tetrahedron Lett. 1992, 33, 3587-3590. (f) Lagu, B. R.; Liotta, D. C. Tetrahedron Lett. 1994, 35, 4485-4488.
12. For 1,4-induction in acetate aldol reactions see: (a) Zibuck, R.; Liverton, N. J.; Smith, A. B. J. Am. Chem. Soc. 1986, 108, 2451-2453. (b) Braun, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 24-37. Paterson, I.; Goodman, J. M.; Isaka, M. Tetrahedreon Lett. 1989, 30, 7121-7124. Trost, B. M.; Urabe, H. J. Org. Chem. 1990, 55, 3982-3983. (e) Roush, W. R.; Bannister, T. D. Tetrahedron Lett. 1992, 33, 3587-3590. (f) Lagu, B. R.; Liotta, D. C. Tetrahedron Lett. 1994, 35, 4485-4488.
13. For 1,4-induction in acetate aldol reactions see: (a) Zibuck, R.; Liverton, N. J.; Smith, A. B. J. Am. Chem. Soc. 1986, 108, 2451-2453. (b) Braun, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 24-37. Paterson, I.; Goodman, J. M.; Isaka, M. Tetrahedreon Lett. 1989, 30, 7121-7124. Trost, B. M.; Urabe, H. J. Org. Chem. 1990, 55, 3982-3983. (e) Roush, W. R.; Bannister, T. D. Tetrahedron Lett. 1992, 33, 3587-3590. (f) Lagu, B. R.; Liotta, D. C. Tetrahedron Lett. 1994, 35, 4485-4488.
14. 2BCl with these methyl ketone substrates is high (>95:5). In certain cases, 9-BBNOTf is nonselective in this enolization process.
15. 4 were also found to give extremely low levels of stereochemical induction.
16. Mg(II), Ti(IV), and Sn(II) enolates were also nonselective.
17. Selectivity and isolated yields for the 1,5-anti product with boron enolate 1 was high regardless of the structure of the aldehyde: isovaleraldehyde (90:10, 88%), isobutyraldehyde (94:6, 84%), pivaldehyde (95:5, 88%), and benzaldehyde (94:6, 88%).
18. This trend has also been noted in the addition of enolsilanes to β-alkoxy aldehydes. See ref 2a.
19. The authors wish to thank Mr. Duke Fitch for carrying out the reaction illustrated in entry 3, Table 2.
20. (a) Evans, D. A.; Calter, M. A. Tetrahedron Lett. 1993, 34, 6871-6874.
21. (b) Evans, D. A.; Fitch, D. J. Org. Chem. 1997, 62, in press.
22. Li, Y.; Padden-Row, M. N.; Houk, K. N. J. Org. Chem. 1990, 55, 481-493.
23. Since submission of this manuscript, a related study has been reported: Paterson, I; Gibson, K. R.; Oballa, R. M. Tetrahedron Lett. 1996, 37, 8585-8588.
24. The author has deposited atomic coordinates for ketone 4f with the Cambridge Crystallographic Date Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
25. (R)-6 amd (S)-6 were prepared in analogy to the Heathcock procedure: (a) Theisen, P. D.; Heathcock, C. H. J. Org. Chem. 1988, 53, 2374-2378. (b) We have found that commerically available 2(R)-and 2(S)-naphthylethanol work well in this esterification process: Evans, D. A.; Black, W. C. J. Am. Chem. Soc. 1993, 115, 4497-4513.
26. (R)-6 amd (S)-6 were prepared in analogy to the Heathcock procedure: (a) Theisen, P. D.; Heathcock, C. H. J. Org. Chem. 1988, 53, 2374-2378. (b) We have found that commerically available 2(R)-and 2(S)-naphthylethanol work well in this esterification process: Evans, D. A.; Black, W. C. J. Am. Chem. Soc. 1993, 115, 4497-4513.