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

S M  Allin; D G  Vaidya; M I  Page; Alexandra Martha Zoya Slawin; Tim Smith

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

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

S M Allin, D G Vaidya, M I Page, Alexandra Martha Zoya Slawin, Tim Smith

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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. (C) 2000 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	2219-2222
Number of pages	4
Journal	Tetrahedron Letters
Volume	41
Issue number	13
DOIs	https://doi.org/10.1016/S0040-4039(00)00128-3
Publication status	Published - 27 Mar 2000

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SDG 3 Good Health and Well-being

Keywords

HIV-1 REVERSE-TRANSCRIPTASE
DERIVATIVES
INHIBITORS

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

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. (C) 2000 Elsevier Science Ltd. All rights reserved.",

keywords = "HIV-1 REVERSE-TRANSCRIPTASE, DERIVATIVES, INHIBITORS",

author = "Allin, \{S M\} and Vaidya, \{D G\} and Page, \{M I\} and Slawin, \{Alexandra Martha Zoya\} and Tim Smith",

note = "Corrigendum appears in Vol.43, issue 1, 01/01/2002: http://dx.doi.org/10.1016/S0040-4039(01)02058-5",

year = "2000",

month = mar,

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doi = "10.1016/S0040-4039(00)00128-3",

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T1 - Highly diastereoselective synthesis and template manipulation of the thiazolo[2,3-a]isoindolin-1-one ring system

AU - Allin, S M

AU - Vaidya, D G

AU - Page, M I

AU - Slawin, Alexandra Martha Zoya

AU - Smith, Tim

N1 - Corrigendum appears in Vol.43, issue 1, 01/01/2002: http://dx.doi.org/10.1016/S0040-4039(01)02058-5

PY - 2000/3/27

Y1 - 2000/3/27

N2 - 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. (C) 2000 Elsevier Science Ltd. All rights reserved.

AB - 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. (C) 2000 Elsevier Science Ltd. All rights reserved.

KW - HIV-1 REVERSE-TRANSCRIPTASE

KW - DERIVATIVES

KW - INHIBITORS

UR - https://www.scopus.com/pages/publications/0034719948

U2 - 10.1016/S0040-4039(00)00128-3

DO - 10.1016/S0040-4039(00)00128-3

M3 - Article

SN - 0040-4039

VL - 41

SP - 2219

EP - 2222

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 13

ER -

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

Abstract

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