Formation of four- to six-membered carbocycles by tandem brook rearrangement-intramolecular Michael reaction

Synlett

Volumn , Issue 6, 1999, Pages 705-708

  Takeda, Kei ^a   Tanaka, Tadashi ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

Acylsilane; Brook rearrangement; Carbocycles; Intramolecular Michael reaction; Tandem reaction

Indexed keywords

ARTICLE; CHEMICAL REACTION; CYCLIZATION; MICHAELIS CONSTANT; SYNTHESIS;

EID: 0033038577     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2737     Document Type: Article

References (13)

1. Little, R. D.; Masjedizadeh, M. R.; Wallquist, O.; McLoughlin, J. I. In Organic Reactions; John Wiley & Sons: New York, 1995; Vol. 47, p 315-552.
2. Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1992; Vol. 9.
3. M. P. Cooke, Jr. J. Org. Chem. 1993, 58, 6833-6837 and references cited therein.
4. For intermolecular Michael reaction of the carbanion generated by Brook rearrangement followed by conversion to copper species, see: Enda, J.; Kuwajima, I. J. Am. Chem. Soc. 1985, 107, 5495-5501.
5. For participation of the carbanion generated by the Brook rearrangement in the intramolecular alkylation to form cyclopropane derivatives, see: Reich, H. J.; Holtan, R. C.; Bolm, C. J. Am. Chem. Soc. 1990, 112, 5609-5617.
6. Brook, A. G. Acc. Chem. Res. 1974, 7, 77-84.
7. Brook, A. G.; Bassindale, A. R. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: New York, 1980; Vol. 2, p 149-221.
8. Takeda, K.; Nakatani, J.; Nakamura, H.; Sako, K.; Yoshii, E.; Yamaguchi, K. Synlett 1993, 841-843.
9. 3Si 256.1495, found 256.1479.
10. Miller, J. A.; Zweifel, G. Synthesis 1981, 288-289.
11. Yoshizaki, H.; Tanaka, T.; Yoshii, E.; Koizumi, T.; Takeda, K. Tetrahedron Lett. 1998, 39, 47-50.
12. 3Si 348.2121, found 348.2091.
13. 2), 77.9 (C-2), 174.2 (C = O).