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

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

Steven M. Allin, Darshan G. Vaidya, Michael I. Page, Alexandra M.Z. Slawin, Tim Smith

School of Applied Sciences

Loughborough University

Research output: Contribution to journal › Article › peer-review

16 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 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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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. ",

author = "Allin, \{Steven M.\} and Vaidya, \{Darshan G.\} and Page, \{Michael I.\} and Slawin, \{Alexandra M.Z.\} and Tim Smith",

year = "2000",

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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, Steven M.

AU - Vaidya, Darshan G.

AU - Page, Michael I.

AU - Slawin, Alexandra M.Z.

AU - Smith, Tim

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.

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.

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

AN - SCOPUS:0034719948

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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