Journal of the American Chemical Society

Sparteine-mediated. alpha.-lithiation of N-BOC-N-methylbenzylamine: Rapid racemization and subsequent deracemization.

M Schlosser, D Limat

Index: Schlosser, Manfred; Limat, Dominique Journal of the American Chemical Society, 1995 , vol. 117, # 49 p. 12342 - 12343

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Citation Number: 59

Abstract

More than a quarter of a century ago, the Nozaki group'studied the asymmetric deprotonation of ethylbenzene using butyllithium in the presence of (-)-sparteine to isolate, after carboxylation, I-phenylpropanoic acid (5 15%) with a maximum enantiomeric excess (ee) of 30%. Sporadically, other investigations of sparteine as a chiral auxiliary were reported? but none of them proved to have a potential for practical development. The ...

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