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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Stereoselectivity
Stereochemistry
Benzoic Acid
X ray crystallography
X Ray Crystallography
Alkylation
Skeleton
Cysteine
Condensation
Esters
Substrates

Cite this

Allin, Steven M. ; Vaidya, Darshan G. ; Page, Michael I. ; Slawin, Alexandra M.Z. ; Smith, Tim. / Highly diastereoselective synthesis and template manipulation of the thiazolo[2,3-a]isoindolin-1-one ring system. In: Tetrahedron Letters. 2000 ; Vol. 41, No. 13. pp. 2219-2222.
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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.; Smith, Tim.

In: Tetrahedron Letters, Vol. 41, No. 13, 27.03.2000, p. 2219-2222.

Research output: Contribution to journalArticle

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