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Stereoselective Conjugate Addition of the Lithium Anion of N-Allyl lmine to Unsaturated Esters: Application to the Enantiospecific Total Synthesis of (-)-Epibatidine

Prasad, Kavirayani R and Uphade, Manoj B (2019) Stereoselective Conjugate Addition of the Lithium Anion of N-Allyl lmine to Unsaturated Esters: Application to the Enantiospecific Total Synthesis of (-)-Epibatidine. In: JOURNAL OF ORGANIC CHEMISTRY, 84 (15). pp. 9648-9660.

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Official URL: https://dx.doi.org/10.1021/acs.joc.9b01340

Abstract

A regio- and diastereoselective conjugate addition of the lithium anion of N-allyl imine (prepared from allylamine and benzophenone) to alpha,beta-unsaturated esters in good yields is reported. The reaction was general and provided the gamma-amino esters resulting from the regioselective C-C bond formation between the alpha-carbon to the nitrogen in the imine and the beta-carbon of the unsaturated ester. Synthetic utility of the formed products was illustrated in the nonracemic total synthesis of the bioactive alkaloid (-)-epibatidine.

Item Type: Journal Article
Additional Information: copyright for this article belongs to AMER CHEMICAL SOC
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 16 Sep 2019 08:57
Last Modified: 16 Sep 2019 08:57
URI: http://eprints.iisc.ac.in/id/eprint/63527

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