Some aspects of intramolecular carbocyclization of methyl (2E)-3-[(1S,2R,5R)-2-({[tert-butyl(dimethyl)-silyl]oxy}methyl)-5-(trimethylsilyl)cyclopent-3-en-1-yl]prop-2-enoate and its derivatives

Abstract

Treatment of methyl (2E)-3-[(1S,2R,5R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-(trimethylsilyl) cyclopent-3-en-1-yl]prop-2-enoate with Bu4NF in THF resulted in intramolecular cyclization with formation of bicyclo[3.1.0]hexene structure. Possible ways of cyclopropane ring closure were discussed. Methyl (2E)-3-[(1R,4R,5S)-5-formyl-4-(trimethylsilyl)cyclopent-2-en-1-yl]prop-2-enoate failed to undergo intramolecular Baylis–Hillman reaction.