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

Allin, Steven M., Vaidya, Darshan G., Page, Michael I., Slawin, Alexandra M.Z. and Smith, Tim (2000) Highly diastereoselective synthesis and template manipulation of the thiazolo[2,3-a]isoindolin-1-one ring system. Tetrahedron Letters, 41 (13). pp. 2219-2222. ISSN 0040-4039

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Abstract

Condensation of 2-acetyl benzoic acid with -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

Item Type: Article
Subjects: Q Science > Q Science (General)
Q Science > QD Chemistry
Schools: School of Applied Sciences
School of Applied Sciences > Biomolecular Sciences Research Centre
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Depositing User: Sara Taylor
Date Deposited: 17 Oct 2008 11:22
Last Modified: 20 Oct 2008 10:16
URI: http://eprints.hud.ac.uk/id/eprint/2263

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