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

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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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Official URL: http://dx.doi.org/10.1016/S0040-4039(00)00128-3

DOI: 10.1016/S0040-4039(00)00128-3

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
Related URLs:	Author
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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