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Stereoselective addition of Grignard reagents to sulfinimines derived from tartrate diol (threitol): Generation of chiral building blocks for the collective total synthesis of lentiginosine, conhydrine and methyldihydropalustramate

Prasad, Kavirayani R and Rangari, Vipin Ashok (2019) Stereoselective addition of Grignard reagents to sulfinimines derived from tartrate diol (threitol): Generation of chiral building blocks for the collective total synthesis of lentiginosine, conhydrine and methyldihydropalustramate. In: TETRAHEDRON, 75 (37).

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Official URL: https://dx.doi.org/10.1016/j.tet.2019.130496

Abstract

A systematic investigation of the addition of Grignard reagents to sulfinimines derived from tartaric acid diol was undertaken. It was observed that the chirality of the inherent tartrate moiety influences the diastereoselectivity of the resultant sulfinamides formed in the reaction. The formed products serve as excellent building blocks for the synthesis of natural products. This has been demonstrated in the collective total synthesis of lentiginosine, (+)-alpha-conhydrine and methyldihydropalustramate.

Item Type: Journal Article
Additional Information: copyright for this article belongs to PERGAMON-ELSEVIER SCIENCE LTD
Keywords: Sulfinimines; Chiral pool; Stereoselective addition; Total synthesis; Alkaloids
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 29 Oct 2019 05:34
Last Modified: 29 Oct 2019 05:34
URI: http://eprints.iisc.ac.in/id/eprint/63722

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