Issue 20, 2003
From the journal:

Chemical Communications

A stereoselective synthesis of anti-γ,δ-alkynyl- and -alkenyl-β-hydroxy-α-amino esters from tin(ii) enolates of glycinate†

Jonathan J. Gridley,a   Michael P. Coogan,a   David W. Knight,*a   K. M. Abdul Malik,a   Christopher M. Sharland,a   Jirada Singkhonrata  and  Siân Williamsa  

* Corresponding authors

a Chemistry Department, Cardiff University, P.O. Box 912, Cardiff, UK
E-mail: knightdw@cf.ac.uk
Fax: 44(0) 2920 874210
Tel: 44(0) 2920 874210

Abstract

Condensations between the tin(II) enolate 11 of ethyl N-tosylglycinate and conjugated ynals 12 and ynones 14 are highly diastereoselective, in favour of the anti-isomers 13 and 15; similar reactions of enals and enones 17 show lower but still useful levels of anti-stereoselectivity.

Graphical abstract: A stereoselective synthesis of anti-γ,δ-alkynyl- and -alkenyl-β-hydroxy-α-amino esters from tin(ii) enolates of glycinate

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Article information

DOI
https://doi.org/10.1039/B306291K
Article type
Communication
Submitted
03 Jun 2003
Accepted
18 Jul 2003
First published
17 Sep 2003

Chem. Commun., 2003, 2550-2551

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A stereoselective synthesis of anti-γ,δ-alkynyl- and -alkenyl-β-hydroxy-α-amino esters from tin(II) enolates of glycinate

J. J. Gridley, M. P. Coogan, D. W. Knight, K. M. A. Malik, C. M. Sharland, J. Singkhonrat and S. Williams, Chem. Commun., 2003, 2550 DOI: 10.1039/B306291K

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