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

Authors
Allin, SM Vaidya, DG Page, MI Slawin, AMZ Smith, T
Citation
Sm. Allin et al., Highly diastereoselective synthesis and template manipulation of the thiazolo[2,3-a]isoindolin-1-one ring system, TETRAHEDR L, 41(13), 2000, pp. 2219-2222
Citations number
15
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
13
Year of publication
2000
Pages
2219 - 2222
Database
ISI
SICI code
0040-4039(20000327)41:13<2219:HDSATM>2.0.ZU;2-2
Abstract
Condensation of 2-acetyl benzoic acid with L-cysteine esters proceeds with extremely high diastereoselectivity to produce the desired thiazolo[2,3-a]i soindolin-1-one products in good yield. The relative stereochemistry of the major diastereoisomer has been determined by X-ray crystallography. Stereo selective enolate alkylation of this substrate has been investigated as a m ethod to manipulate the ring skeleton, and was found to proceed with up to exclusive levels of stereoselectivity. (C) 2000 Elsevier Science Ltd. All r ights reserved.