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Panduwawala TD, Iqbal S, Tirfoin R, et al. Chemoselectivity and stereoselectivity of cyclisation pathways leading to bicyclic tetramates controlled by ring-chain tautomerisation in thiazolidines. Org Biomol Chem. 2016;14(19):4464-78doi: 10.1039/c6ob00557h.
Panduwawala, T. D., Iqbal, S., Tirfoin, R., & Moloney, M. G. (2016). Chemoselectivity and stereoselectivity of cyclisation pathways leading to bicyclic tetramates controlled by ring-chain tautomerisation in thiazolidines. Organic & biomolecular chemistry, 14(19), 4464-78. https://doi.org/10.1039/c6ob00557h
Panduwawala, Tharindi D, et al. "Chemoselectivity and stereoselectivity of cyclisation pathways leading to bicyclic tetramates controlled by ring-chain tautomerisation in thiazolidines." Organic & biomolecular chemistry vol. 14,19 (2016): 4464-78. doi: https://doi.org/10.1039/c6ob00557h
Panduwawala TD, Iqbal S, Tirfoin R, Moloney MG. Chemoselectivity and stereoselectivity of cyclisation pathways leading to bicyclic tetramates controlled by ring-chain tautomerisation in thiazolidines. Org Biomol Chem. 2016 May 11;14(19):4464-78. doi: 10.1039/c6ob00557h. PMID: 27089842.
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Org Biomol Chem. 2016 May 11;14(19):4464-78. doi: 10.1039/c6ob00557h.

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

Organic & biomolecular chemistry

Tharindi D Panduwawala, Sarosh Iqbal, Rémi Tirfoin, Mark G Moloney

Affiliations

  1. Department of Chemistry, Chemistry Research Laboratory, The University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK. [email protected].

PMID: 27089842 DOI: 10.1039/c6ob00557h

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.

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