EFFICIENT AND PRACTICAL SYNTHESIS OF OPTICALLY-ACTIVE 5-T-BUTYLDIMETHYLSILOXY-2-CYCLOHEXENONE AS A CONVENIENT CHIRAL 2,5-CYCLOHEXADIENONE SYNTHON

Authors
HIKICHI S HAREAU GPJ SATO F
Citation
S. Hikichi et al., EFFICIENT AND PRACTICAL SYNTHESIS OF OPTICALLY-ACTIVE 5-T-BUTYLDIMETHYLSILOXY-2-CYCLOHEXENONE AS A CONVENIENT CHIRAL 2,5-CYCLOHEXADIENONE SYNTHON, Tetrahedron letters, 38(48), 1997, pp. 8299-8302
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
48
Year of publication
1997
Pages
8299 - 8302
Database
ISI
SICI code
0040-4039(1997)38:48<8299:EAPSOO>2.0.ZU;2-M
Abstract
An efficient and practical method for the preparation of optically act ive 5-t-butyldimethylsiloxy-2-cyclohexenone (3), a convenient chiral 2 ,5-cyclohexadienone synthon, from readily available ethyl 4-chloro-3-h ydroxy-butyrate (7) has been developed where Ti(II)-mediated intramole cular nucleophilic acyl substitution and FeCl3-mediated ring expansion are the key reactions. The synthesis of racemic 6-t-butyldimethylsilo xy-2-cycloheptenone (10), a potential 2,6-cycloheptadienone synthon, i s also described. (C) 1997 Elsevier Science Ltd.