Synthesis of optically active 5-(tert-butyldimethylsiloxy)-2-cyclohexenone and its 6-substituted derivatives as useful chiral building blocks for the synthesis of …

GPJ Hareau, M Koiwa, S Hikichi…

Index: Hareau, Georges P.-J.; Koiwa, Masakazu; Hikichi, Shinichi; Sato, Fumie Journal of the American Chemical Society, 1999 , vol. 121, # 15 p. 3640 - 3650

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Citation Number: 87

Abstract

Optically active 5-(tert-butyldimethylsiloxy)-2-cyclohexenone (1) and its 6-substituted derivatives 2a, b were synthesized from the readily available optically active ethyl 3-(tert- butyldimethylsiloxy)-5-hexenoate (4), where the Ti (II)-mediated intramolecular nucleophilic acyl substitution reaction and the FeCl3-mediated ring expansion reaction of a 1- hydroxybicyclo [3.1. 0] hexane are the key reactions. The enone 1 reacted with higher- ...