Neighboring carbonyl group assisted oxyacetoxylation of propargylic carboxylates with retention of chirality under metal free condition

Pradhan, Tapas R. and Mohapatra, Debendra K. 2019. Neighboring carbonyl group assisted oxyacetoxylation of propargylic carboxylates with retention of chirality under metal free condition. Advanced Synthesis & Catalysis 361 (15) , pp. 3605-3611. 10.1002/adsc.201900314

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Abstract

A metal-free oxyacetoxylation method of primary, secondary and tertiary propargylic carboxylates with retention of chirality was presented. The reaction proceeds through the intramolecular nucleophilic attack of the neighboring carbonyl group on an alkynyliodonium intermediate. The process is general with broad substrate scope and is amenable for application to a variety of propargyl carboxylates including those obtained from natural products. Insight into the mechanistic pathway by isotopic labelling (using H2O18 and D2O) and controlled experiments confirmed.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Publisher:	Wiley
ISSN:	1615-4150
Last Modified:	26 Jan 2024 14:45
URI:	https://orca.cardiff.ac.uk/id/eprint/165580

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