Nucleophilic synthesis of enantiopure 2-(tributylstannyl)pyrrolidines and piperidines
by Gawley, Robert E.; Barolli, Graciela; Madan, Sachin; Saverin, Michele; O'Connor, S.
trans-Cumylcyclohexanol (TCC) is used as a chiral auxiliary for the stereoselective addition of tributyltinlithium to N-acylpyrrolidinium/piperidinium ion with 70-80% diastereoselectivity at 0degreesC. After removal of the minor diastereomer by radial chromatography, enantiopure N-methyl-2-(tributylstannyl)pyrrolidine and piperidine were produced by reductive removal of the auxiliary. (C) 2003 Elsevier Ltd. All rights reserved.
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