Kinetic resolution of tert-butyl (RS)-3-alkylcyclopentene-1-carboxylates for the synthesis of homochiral 3-alkyl-cispentacin and 3-alkyl-transpentacin derivatives

ME Bunnage, SG Davies, RM Parkin…

Index: Bunnage, Mark E.; Davies, Stephen G.; Parkin, Richard M.; Roberts, Paul M.; Smith, Andrew D.; Withey, Jonathan M. Organic and Biomolecular Chemistry, 2004 , vol. 2, # 22 p. 3337 - 3354

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Citation Number: 27

Abstract

High levels of stereocontrol are observed in the conjugate addition of lithium dibenzylamide to tert-butyl (RS)-3-alkylcyclopentene-1-carboxylates (alkyl= Et, Bn), with addition occurring exclusively anti-to the 3-alkyl substituent. Treatment of a range of tert-butyl (RS)-3- alkylcyclopentene-1-carboxylates (alkyl= Et, Bn, iPr, tBu) with lithium (RS)-N-benzyl-N-α- methylbenzylamide indicates that good enantiorecognition is observed (E> 80) in their ...