Studies on the mechanism and origin of stereoselective opening of chiral dioxane acetals

SE Denmark, NG Almstead

Index: Denmark, Scott E.; Almstead, Neil G. Journal of the American Chemical Society, 1991 , vol. 113, # 21 p. 8089 - 8110

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Citation Number: 161

Abstract

Abstract: A systematic examination of the mechanism and origin of stereoselection in the reaction of dioxane acetals with allyltrimethylsilane was undertaken. Experimental tests for two limiting mechanisms, synchronous (SN2-like) and dissociative (SN1-like) substitution processes, were investigated. The meso 2, 4, 6-trisubstituted 1, 3-dioxane acetals cis-and trans-1 provided an interesting opportunity to test the timing of bond breaking and making ...