5 (R)-Methyl-1-(chloromethyl)-2-pyrrolidinone: a new reagent for the determination of enantiomeric composition of alcohols

MB Smith, BT Dembofsky, YC Son

Index: Smith, Michael B.; Dembofsky, Bruce T.; Son, Young Chan Journal of Organic Chemistry, 1994 , vol. 59, # 7 p. 1719 - 1725

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Citation Number: 37

Abstract

We have prepared a new chiral nonracemic reagent (5 (R)-methyl-l-(chloromethyl)-2- pyrrolidinone) in enantiopure form that reacts with alcohols containing a stereogenic center to produce diastereomeric N-(alkoxymethyl)-2-pyrrolidinone derivatives. These derivatives exhibit large and easily observed diastereotopic signals in the proton NMR that allow direct determination of diastereomeric ratio (% dr) for the product.