Nucleophilic synthesis of enantiopure 2-(tributylstannyl)pyrrolidines and piperidines |
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| Authors: | Robert E. Gawley Graciela Barolli Michele Saverin |
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| Affiliation: | a Department of Chemistry, University of Miami, Coral Gables, FL 33124, USA
b Department of Chemistry and Biochemistry, University of Arkansas, Fayetteville, AR 72701, USA |
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| Abstract: | 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. |
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| Keywords: | (Stannanyl)pyrrolidines TCC N-Acyliminium ion Asymmetric synthesis |
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