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Stereoselective Addition of a Lithium Anion of 1,1-Diphenyl-2-aza-pentadiene to Sulfinimines: Application to the Synthesis of (-)-Epiquinamide

Uphade, Manoj B and Reddy, Arava Amaranadha and Khandare, Sopan P and Prasad, Kavirayani R (2019) Stereoselective Addition of a Lithium Anion of 1,1-Diphenyl-2-aza-pentadiene to Sulfinimines: Application to the Synthesis of (-)-Epiquinamide. In: ORGANIC LETTERS, 21 (22). pp. 9109-9113.

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Official URL: http://dx.doi.org/10.1021/acs.orglett.9b03507

Abstract

The addition of a lithium anion of diphenylallylimine to nonracemic sulfinimines was investigated. It was found that the reaction with sulfinimines derived from aliphatic aldehydes afforded the products with excellent diastereoselectivity (>99:1), furnishing the product vicinal diamines in very good yields. Application of the formed product vicinal diamines was demonstrated in the total synthesis of the natural product (-)-epiquinamide.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to AMER CHEMICAL SOC
Keywords: ASYMMETRIC-SYNTHESIS; (+)-EPIQUINAMIDE; ACCESS
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 16 Dec 2019 11:41
Last Modified: 16 Dec 2019 11:41
URI: http://eprints.iisc.ac.in/id/eprint/64055

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