Highly diastereoselective synthesis and template manipulation of the thiazolo[2,3-a]isoindolin-1-one ring system

Steven M. Allin, Darshan G. Vaidya, Michael I. Page, Alexandra M.Z. Slawin, Tim Smith

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Condensation of 2-acetyl benzoic acid with L-cysteine esters proceeds with extremely high diastereoselectivity to produce the desired thiazolo[2,3- a]isoindolin-1-one products in good yield. The relative stereochemistry of the major diastereoisomer has been determined by X-ray crystallography. Stereoselective enolate alkylation of this substrate has been investigated as a method to manipulate the ring skeleton, and was found to proceed with up to exclusive levels of stereoselectivity. 

Original languageEnglish
Pages (from-to)2219-2222
Number of pages4
JournalTetrahedron Letters
Volume41
Issue number13
DOIs
Publication statusPublished - 27 Mar 2000

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