A regio- and stereoselective α-methylation of γ,δ-epoxy-α,β-unsaturated esters with a Me2Zn-CuCN reagent

Chemical Communications

Volumn , Issue 17, 2002, Pages 1970-1971

  Hirai, Atsushi ^a   Matsui, Atsushi ^a   Komatsu, Kei ^a   Tanino, Keiji ^a   Miyashita, Masaaki ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER COMPLEX; EPOXIDE; ESTER DERIVATIVE; METHYL GROUP; REAGENT; ZINC COMPLEX;

ARTICLE; INFRARED SPECTROSCOPY; METHYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0036966948     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b205957f     Document Type: Article

References (9)

1. B. M. Kim, S. F. Williams and S. Masamune, in Comprehensive Organic Synthesis, Additions to C-X p-Bonds Part 2, ed. C. H. Heathcock, Pergamon Press, Oxford, 1991, vol. 2. ch. 1.7.
2. M. Miyashita, M. Hoshino and A. Yoshikoshi, J. Org. Chem., 1991, 56, 6483; M. Miyazawa, N. Ishibashi, S. Oonuma and M. Miyashita, Tetrahedron Lett., 1997, 38, 3419; N. Ishibashi, M. Miyazawa and M. Miyashita, Tetrahedron Lett., 1998, 39, 3775.
3. M. Miyashita, M. Hoshino and A. Yoshikoshi, J. Org. Chem., 1991, 56, 6483; M. Miyazawa, N. Ishibashi, S. Oonuma and M. Miyashita, Tetrahedron Lett., 1997, 38, 3419; N. Ishibashi, M. Miyazawa and M. Miyashita, Tetrahedron Lett., 1998, 39, 3775.
4. M. Miyashita, M. Hoshino and A. Yoshikoshi, J. Org. Chem., 1991, 56, 6483; M. Miyazawa, N. Ishibashi, S. Oonuma and M. Miyashita, Tetrahedron Lett., 1997, 38, 3419; N. Ishibashi, M. Miyazawa and M. Miyashita, Tetrahedron Lett., 1998, 39, 3775.
5. T. Ibuka, M. Tanaka, H. Nemoto and Y. Yamamoto, Tetrahedron, 1989, 45, 435.
6. T. Ibuka, T. Nakao, S. Nishii and Y. Yamamoto, J. Am. Chem. Soc., 1986, 108, 7420 and references therein.
7. N2′ reaction with allyl halides: E. Nakamura, K. Sekiya, M. Arai and S. Aoki, J. Am. Chem. Soc., 1989, 111, 3091.
8. 4 and concentrated in vacuo. Purification by silica gel chromatography (hexane-ether; 1:1) afforded the α-methylated product (α:γ = 90:10) as a pale yellow oil (0.95 g, 86% yield). The reaction with a catalytic amount of CuCN was also performed in a similar manner as noted above.
9. M. Frohn, M. Dalkiewicz, Y. Tu, Z.-X. Wang and Y. Shi, J. Org. Chem., 1998, 63, 2948.