The Journal of organic chemistry

Cyclobutanones through SN i'Ring Closure, a Mechanistic Study

MA Lovchik, A Goeke, G Fráter

Index: Lovchik, Martin A.; Goeke, Andreas; Frater, Georg Journal of Organic Chemistry, 2007 , vol. 72, # 7 p. 2427 - 2433

Full Text: HTML

Citation Number: 12

Abstract

Mechanistic studies on the intramolecular nucleophilic substitution with allylic rearrangement (SN i'reaction) and a new stereoselective access to substituted cyclobutanones are reported. 4, 4-Dialkyl-5-oxohex-2 E-en-1-yl methanesulfonates 4 were converted to 2, 2-dialkyl-3-vinylcyclobutanones 6 by SN i'ring closure. The stereochemical analysis of the reaction was achieved through ring closure of (6 S)-6-chloro-3, 3- ...