An isothiourea-catalyzed asymmetric [2, 3]-rearrangement of allylic ammonium ylides

…, DSB Daniels, AMZ Slawin, AD Smith

Index: West, Thomas H.; Daniels, David S. B.; Slawin, Alexandra M. Z.; Smith, Andrew D. Journal of the American Chemical Society, 2014 , vol. 136, # 12 p. 4476 - 4479

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Citation Number: 32

Abstract

Benzotetramisole promotes the catalytic asymmetric [2, 3]-rearrangement of allylic quaternary ammonium salts (either isolated or prepared in situ from p-nitrophenyl bromoacetate and the corresponding allylic amine), generating syn-α-amino acid derivatives with excellent diastereo-and enantioselectivity (up to> 95: 5 dr; up to> 99% ee).