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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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
Publication:	JOURNAL OF ORGANIC CHEMISTRY
Publisher:	AMER CHEMICAL SOC
Additional Information:	copyright for this article belongs to AMER CHEMICAL SOC
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
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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