Generation and asymmetric Michael addition reaction of chirally N- protected α-aminoalkyl cyanocuprates

Tetrahedron Letters

Volumn 41, Issue 3, 2000, Pages 345-349

  Tomoyasu, Takahiro ^a   Tomooka, Katsuhiko ^a   Nakai, Takeshi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Amino ketones; Asymmetric synthesis; Copper reagents; Michael reaction; Transmetalation

Indexed keywords

COPPER DERIVATIVE; KETONE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034650648     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02059-6     Document Type: Article

References (26)

1. For reviews, see: (a) Krause, N.; Gerold, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 186-204. (b) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771-806. (c) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1992.
2. For reviews, see: (a) Krause, N.; Gerold, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 186-204. (b) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771-806. (c) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1992.
3. For reviews, see: (a) Krause, N.; Gerold, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 186-204. (b) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771-806. (c) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1992.
4. (a) Linderman, R. J.; Griedel, B. D. J. Org. Chem. 1991, 56, 5491-5493.
5. (b) Linderman, R. J.; Griedel, B. D. J. Org. Chem. 1990, 55, 5428-5430.
6. To our knowledge, only a few examples of racemic α-amino alkylcyanocuprate are reported: (a) Dieter, R. K.; Sadanandan, E. V. J. Org. Chem. 1997, 62, 3798-3799. (b) Dieter, R. K.; Alexander, C. W. Synlett 1993, 407-409. (c) Dieter, R. K.; Alexander, C. W. Tetrahedron Lett. 1992, 33, 5693-5696.
7. To our knowledge, only a few examples of racemic α-amino alkylcyanocuprate are reported: (a) Dieter, R. K.; Sadanandan, E. V. J. Org. Chem. 1997, 62, 3798-3799. (b) Dieter, R. K.; Alexander, C. W. Synlett 1993, 407-409. (c) Dieter, R. K.; Alexander, C. W. Tetrahedron Lett. 1992, 33, 5693-5696.
8. To our knowledge, only a few examples of racemic α-amino alkylcyanocuprate are reported: (a) Dieter, R. K.; Sadanandan, E. V. J. Org. Chem. 1997, 62, 3798-3799. (b) Dieter, R. K.; Alexander, C. W. Synlett 1993, 407-409. (c) Dieter, R. K.; Alexander, C. W. Tetrahedron Lett. 1992, 33, 5693-5696.
9. Schöllkopf et al. have reported the asymmetric conjugate addition reaction of chiral bislactim-ether cuprates: Schöllkopf, U.; Pettig, D.; Schulze, E.; Klinge, M.; Egert, E.; Benecke, B.; Noltemeyer, M. Angew. Chem., Int. Ed. Engl. 1988, 27, 1194-1195.
10. Beak et al. have reported the asymmetric conjugate addition reactions of enantio-enriched N-Boc anilino benzylic and allylic organolithium species: Park, Y. S.; Weisenburger, G. A.; Beak, P. J. Am. Chem. Soc. 1997, 119, 10537-10538.
11. (a) Gawley, R. E.; Zhang, Q. J. Org. Chem. 1995, 60, 5763-5769
12. (b) Burchat, A. F.; Chong, J. M.; Park, S. B. Tetrahedron Lett. 1993, 34, 51-54
13. (c) Chong, J. M.; Park, S. B. J. Org. Chem. 1992, 57, 2220-2222
14. (d) Gawley, R. E.; Rein, K. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol 1, pp. 459-485
15. (e) Gawley, R. E.; Rein, K. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol 3, pp. 65-83.
16. (a)Pearson, W.H., Lindbeck A.C., Kampf J.W. J. Am. Chem. Soc. 1993, 115, 2622-2636.
17. (b) Pearson, W. H.; Lindbeck, A. C. J. Am. Chem. Soc. 1991, 113, 8546-8548.
18. Recently, we have reported the synthetic utility of the chiral α-amino organolithiums (B) in the context of asymmetric synthesis of α-amino ketones and β-amino alcohols: Tomoyasu, T.; Tomooka, K.; Nakai, T. Synlett 1998, 1147-1149.
19. The presence of TMSCl is essential for this reaction. In the absence of TMSCl, only a destannylated product was obtained. For a TMSCl effect on the conjugate addition, see: Bertz, S. H.; Miao, G.; Rossiter, B. E.; Snyder, J. P. J. Am. Chem. Soc. 1995, 117, 11023-11024, and references cited therein.
20. 3, 75 MHz) δ 10.6, 23.8, 25.1, 27.0, 35.6, 38.8, 40.6, 56.8, 66.6, 70.7, 127.9, 128.0, 128.4, 136.5, 156.3.
21. In the absence of CuCN, the reaction of alkyllithium (R)-2 with acrolein was found to afford 71% yield of the 1,2-adduct as a mixture of the two epimers due to the α-hydroxy chiral center.
22. 3 of 6: 2.04 for the major isomer and 2.13 for the minor isomer.
23. 3, Z=2. A total of 1673 reflections (h,k,±l) were collected in the range 6°<2θ<50° with 1189 having I a;(I) being used in the structural refinement by full-matrix least-squares techniques (198 variables) using the TEXSAN crystallographic package from Molecular Structures Corporation.
24. Linderman et al. have reported that the addition reaction of enantio-defined α-alkoxyalkylcopper reagents with α,β-enones occurs predominantly with retention of configuration at the carbanionic stereocenter (Ref. 2).
25. It is still hard to propose a transition-state model to rationalize the high diastereoselectivity over the double bond, because the mechanism of the cuprate addition reaction itself remains unsettled.
26. The assignment of the configuration of the newly-formed chiral center of 10 has not been made yet, although R-configuration is highly expected.