Issue 19, 2016

Chemoselectivity and stereoselectivity of cyclisation pathways leading to bicyclic tetramates controlled by ring-chain tautomerisation in thiazolidines

Abstract

Chemoselective Dieckmann cyclisation reactions on N-malonyl thiazolidine templates derived from cysteine and pivaldehyde or aromatic aldehydes may be used to access bicyclic tetramates, for which different pathways operate as a result of differing ring-chain tautomeric behaviour of the respective intermediate imines.

Graphical abstract: Chemoselectivity and stereoselectivity of cyclisation pathways leading to bicyclic tetramates controlled by ring-chain tautomerisation in thiazolidines

Supplementary files

Article information

Article type
Paper
Submitted
14 Mar 2016
Accepted
12 Apr 2016
First published
12 Apr 2016

Org. Biomol. Chem., 2016,14, 4464-4478

Author version available

Chemoselectivity and stereoselectivity of cyclisation pathways leading to bicyclic tetramates controlled by ring-chain tautomerisation in thiazolidines

T. D. Panduwawala, S. Iqbal, R. Tirfoin and M. G. Moloney, Org. Biomol. Chem., 2016, 14, 4464 DOI: 10.1039/C6OB00557H

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