Vanadium (II)-promoted cyclization of 5, 6-enals or 5, 6-ynals. A stereoselective approach to trans-2-alkyl-or trans-2-alkylidenecyclopentanols

T Inokuchi, H Kawafuchi, S Torii

Index: Inokuchi, Tsutomu; Kawafuchi, Hiroyuki; Torii, Sigeru Journal of Organic Chemistry, 1991 , vol. 56, # 16 p. 4983 - 4985

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Citation Number: 31

Abstract

In order to gain more insight into the mechanistic as-pects leading to the trans arrangement from the E olefin la, we examined the reductive coupling of the 2 isomer 1b. lo The reaction proceeded rather slowly compared with the E isomer la and turned out to produce the pinacol4b as a major product (50% yield) along with a mixture of 2b (12%), carbinol 3b (9%), and y-lactone 5 (5%). This result probably suggests that the trapping of the vanadium ...