Tetrahedron letters

Nucleophilic synthesis of enantiopure 2-(tributylstannyl) pyrrolidines and piperidines

…, G Barolli, S Madan, M Saverin, S O'Connor

文献索引：Gawley, Robert E.; Barolli, Graciela; Madan, Sachin; Saverin, Michele; O'Connor, Sean Tetrahedron Letters, 2004 , vol. 45, # 8 p. 1759 - 1761

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被引用次数: 17

摘要

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 0° C. 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.