Unexpected cis-selective 1,4-addition reaction of lower order cyanocuprates to optically active 5-(tert-butyldimethylsiloxy)-2-cyclohexenone

Angewandte Chemie - International Edition

Volumn 37, Issue 15, 1998, Pages 2099-2101

  Hareau Vittini, Georges ^a   Hikichi, Shinichi ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Cuprates; Enones; Nucleophilic additions; Reaction mechanisms; Synthetic methods

Indexed keywords

EID: 0032541295     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980817)37:15<2099::AID-ANIE2099>3.0.CO;2-U     Document Type: Article

References (27)

1. S. Hikichi, G. P-J. Hareau, F. Sato, Tetrahedron Lett. 1997, 38, 8299-8302.
2. For other chiral 2,5-cyclohexadienone synthons, see a) M. Asaoka, K. Shima, H. Takei, Tetrahedron Lett. 1987, 28, 5669-5672; M. Asaoka, H. Takei, J. Synth. Org. Chem. Jpn 1990, 48, 216-228; b) S. Takano, Y. Higashi, T. Kamikubo, M. Moriya, K. Ogasawara, Synthesis 1993, 948-950; K. Ogasawara, Pure Appl. Chem. 1994, 66, 2119-2122.
3. For other chiral 2,5-cyclohexadienone synthons, see a) M. Asaoka, K. Shima, H. Takei, Tetrahedron Lett. 1987, 28, 5669-5672; M. Asaoka, H. Takei, J. Synth. Org. Chem. Jpn 1990, 48, 216-228; b) S. Takano, Y. Higashi, T. Kamikubo, M. Moriya, K. Ogasawara, Synthesis 1993, 948-950; K. Ogasawara, Pure Appl. Chem. 1994, 66, 2119-2122.
4. For other chiral 2,5-cyclohexadienone synthons, see a) M. Asaoka, K. Shima, H. Takei, Tetrahedron Lett. 1987, 28, 5669-5672; M. Asaoka, H. Takei, J. Synth. Org. Chem. Jpn 1990, 48, 216-228; b) S. Takano, Y. Higashi, T. Kamikubo, M. Moriya, K. Ogasawara, Synthesis 1993, 948-950; K. Ogasawara, Pure Appl. Chem. 1994, 66, 2119-2122.
5. For other chiral 2,5-cyclohexadienone synthons, see a) M. Asaoka, K. Shima, H. Takei, Tetrahedron Lett. 1987, 28, 5669-5672; M. Asaoka, H. Takei, J. Synth. Org. Chem. Jpn 1990, 48, 216-228; b) S. Takano, Y. Higashi, T. Kamikubo, M. Moriya, K. Ogasawara, Synthesis 1993, 948-950; K. Ogasawara, Pure Appl. Chem. 1994, 66, 2119-2122.
6. Lower order lithium cyanocuprates ([RCuCNLi]): a) J. P. Gorlier, L. Hamon, J. Levisalles, J. Chem. Soc. Chem. Commun. 1973, 88; b) R.-D. Acker, Tetrahedron Lett. 1977, 3407-3410; c) L. Hamon, J. Levisalles, J. Organomet. Chem. 1983, 251, 133-138.
7. Lower order lithium cyanocuprates ([RCuCNLi]): a) J. P. Gorlier, L. Hamon, J. Levisalles, J. Chem. Soc. Chem. Commun. 1973, 88; b) R.-D. Acker, Tetrahedron Lett. 1977, 3407-3410; c) L. Hamon, J. Levisalles, J. Organomet. Chem. 1983, 251, 133-138.
8. Lower order lithium cyanocuprates ([RCuCNLi]): a) J. P. Gorlier, L. Hamon, J. Levisalles, J. Chem. Soc. Chem. Commun. 1973, 88; b) R.-D. Acker, Tetrahedron Lett. 1977, 3407-3410; c) L. Hamon, J. Levisalles, J. Organomet. Chem. 1983, 251, 133-138.
9. The conjugate addition of organocuprates to 5-substiluted-2-cyclohexenones yields generally a very high proportion of trans-adduct; see the following reviews and references therein: Y. Yamamoto, Methods Org. Chem. (Houben-Weyl) 4th ed., Vol. E21b, 1995, pp. 2041-2067; B. H. Lipshutz, Comprehensive Organic Synthesis, Vol. 1 (Eds.: B. M. Trost, I. Fleming, S. L. Schreiber), Pergamon, Oxford, 1991, pp. 107-138; J. A. Kozlowski, Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhock), Pergamon, Oxford, 1991, pp. 169-198.
10. The conjugate addition of organocuprates to 5-substiluted-2-cyclohexenones yields generally a very high proportion of trans-adduct; see the following reviews and references therein: Y. Yamamoto, Methods Org. Chem. (Houben-Weyl) 4th ed., Vol. E21b, 1995, pp. 2041-2067; B. H. Lipshutz, Comprehensive Organic Synthesis, Vol. 1 (Eds.: B. M. Trost, I. Fleming, S. L. Schreiber), Pergamon, Oxford, 1991, pp. 107-138; J. A. Kozlowski, Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhock), Pergamon, Oxford, 1991, pp. 169-198.
11. The conjugate addition of organocuprates to 5-substiluted-2-cyclohexenones yields generally a very high proportion of trans-adduct; see the following reviews and references therein: Y. Yamamoto, Methods Org. Chem. (Houben-Weyl) 4th ed., Vol. E21b, 1995, pp. 2041-2067; B. H. Lipshutz, Comprehensive Organic Synthesis, Vol. 1 (Eds.: B. M. Trost, I. Fleming, S. L. Schreiber), Pergamon, Oxford, 1991, pp. 107-138; J. A. Kozlowski, Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhock), Pergamon, Oxford, 1991, pp. 169-198.
12. M. Asaoka, K. Takenouchi, H. Takei, Chem. Lett. 1988, 921-922.
13. 2] indicate that the reagents have been prepared stoichiometrically by mixing CuCN and RLi in a ratio of 1:1 and 1:2, respectively.
14. The chemical shift of CH-OTBS appears at around δ = 3.8 for cis-2 and δ = 4.4 for trans-2.
15. L. Dumortier, J. Carda, J. Van der Eyken, G Snatzke, Tetrahedron: Asymmetry 1991, 2, 789-792; M. Suemune, M. Takahashi, S. Maeda, Z.-F. Xie, K. Sakai, Tetrahedron: Asymmetry 1990, 1, 425-428.
16. L. Dumortier, J. Carda, J. Van der Eyken, G Snatzke, Tetrahedron: Asymmetry 1991, 2, 789-792; M. Suemune, M. Takahashi, S. Maeda, Z.-F. Xie, K. Sakai, Tetrahedron: Asymmetry 1990, 1, 425-428.
17. S. J. Danishefsky, B. Simoneau, J. Am. Chem. Soc. 1989, 111, 2599-2604.
18. A selectivity of 92:8 in favor of the cis isomer has been reported on a 4-oxv-substituted spirocyclohexenone: E. J. Corey, N. W. Boaz, Tetrahedron Lett. 1985, 26, 6015-6018. cis-Michael-type addition has been observed on 4-oxy-substituted-2-cyclohexenone: L. O. Jeroncic, M. P. Cabal, S. J. Danishefsky, J. Org. Chem. 1991, 56, 387-395.
19. A selectivity of 92:8 in favor of the cis isomer has been reported on a 4-oxv-substituted spirocyclohexenone: E. J. Corey, N. W. Boaz, Tetrahedron Lett. 1985, 26, 6015-6018. cis-Michael-type addition has been observed on 4-oxy-substituted-2-cyclohexenone: L. O. Jeroncic, M. P. Cabal, S. J. Danishefsky, J. Org. Chem. 1991, 56, 387-395.
20. E. J. Corey, F. J. Hannon, N. W. Boaz, Tetrahedron 1989, 45, 545-555; E. J. Corey, F. J. Hannon, Tetrahedron Lett. 1990, 31, 1393-1396.
21. E. J. Corey, F. J. Hannon, N. W. Boaz, Tetrahedron 1989, 45, 545-555; E. J. Corey, F. J. Hannon, Tetrahedron Lett. 1990, 31, 1393-1396.
22. For some recent progress on the mechanism of the 1,4-addition of cuprates to enones, see N. Krauze, J. Org. Chem. 1992, 57, 3509-3512; A. S. Vellekoop, R. A. J. Smith, J. Am. Chem. Soc. 1994, 116, 2902-2913; J. P. Snyder, J. Am. Chem. Soc. 1995, 117, 11025-11026; K. Nilsson, C. Ullenius, N. Krause, J. Am. Chem. Soc. 1996, 118, 4194-4195, and references therein.
23. For some recent progress on the mechanism of the 1,4-addition of cuprates to enones, see N. Krauze, J. Org. Chem. 1992, 57, 3509-3512; A. S. Vellekoop, R. A. J. Smith, J. Am. Chem. Soc. 1994, 116, 2902-2913; J. P. Snyder, J. Am. Chem. Soc. 1995, 117, 11025-11026; K. Nilsson, C. Ullenius, N. Krause, J. Am. Chem. Soc. 1996, 118, 4194-4195, and references therein.
24. For some recent progress on the mechanism of the 1,4-addition of cuprates to enones, see N. Krauze, J. Org. Chem. 1992, 57, 3509-3512; A. S. Vellekoop, R. A. J. Smith, J. Am. Chem. Soc. 1994, 116, 2902-2913; J. P. Snyder, J. Am. Chem. Soc. 1995, 117, 11025-11026; K. Nilsson, C. Ullenius, N. Krause, J. Am. Chem. Soc. 1996, 118, 4194-4195, and references therein.
25. For some recent progress on the mechanism of the 1,4-addition of cuprates to enones, see N. Krauze, J. Org. Chem. 1992, 57, 3509-3512; A. S. Vellekoop, R. A. J. Smith, J. Am. Chem. Soc. 1994, 116, 2902-2913; J. P. Snyder, J. Am. Chem. Soc. 1995, 117, 11025-11026; K. Nilsson, C. Ullenius, N. Krause, J. Am. Chem. Soc. 1996, 118, 4194-4195, and references therein.
26. For the synthesis of optically active 5-substituted cyclohexenones, see J. B. Schwarz, P. N. Devine, A. I. Meyers, Tetrahedron 1997, 53, 8795-8806, and references therein.
27. CuCN was purchased from Koso Chemical Co., Ltd. Tokyo, Japan, and was used without further purification. Angew. Chem. Int. Ed. 1998. 37. No. 15