Asymmetric induction in the Claisen rearrangement of N-allylketene N, O-acetals

…, OHW Decker, H Hope, MD Yanuck

Index: Kurth, Mark J.; Decker, Owen H. W.; Hope, Hakon; Yanuck, Michael D. Journal of the American Chemical Society, 1985 , vol. 107, # 2 p. 443 - 448

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Citation Number: 57

Abstract

Abstract: Asymmetric CC bond formation via the diastereoselective aza-Claisen rearrangement of N-allylketene N, O-acetal 1 is described. Diastereoselection noted for rearrangement 1-2 ranges from 84% to 96% and is a consequence of complete (2)-N, Oacetal olefin selectivity in 1, high C,-si-face selectivity in the rearrangement of 1 to 2, and the absence of C, epimerization in oxazoline 2. Experiments which establish the steric ...