Synthesis of γ-acetoxy β-keto esters through regioselective hydration of γ-acetoxy-α,β-alkynoates

Pradhan, Tapas R. ORCID: https://orcid.org/0000-0003-1480-7799, Mendhekar, Kishor L. and Mohapatra, Debendra K. 2015. Synthesis of γ-acetoxy β-keto esters through regioselective hydration of γ-acetoxy-α,β-alkynoates. The Journal of Organic Chemistry 80 (11) , 5517–5531. 10.1021/acs.joc.5b00400

Full text not available from this repository.

Abstract

The Au(I)-catalyzed regioselective hydration of γ-acetoxy-α,β-acetylinic ester by the assistance of a neighboring carbonyl group has been developed. Varieties of simple primary, secondary, and tertiary γ-acetoxy-α,β-acetylinic esters, even those bearing sensitive functional group in the remote reaction sites, are selectively hydrated to the corresponding β-keto esters. The reaction tolerates a wide variety of other carboxylates, such as benzoates, propionates, acrylates, and pivalates, including chiral carboxylates with retention of the configuration. The broad substrate scope, including the derivatization of complex natural products and neutral and open air conditions, makes this atom economical approach very practical. 18O labeling experiments disclose that the oxygen transposition occurs from the carboxylate group to the triple bond, not from water.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Publisher:	American Chemical Society
ISSN:	0022-3263
Last Modified:	16 May 2024 01:40
URI:	https://orca.cardiff.ac.uk/id/eprint/165584

Actions (repository staff only)

Edit Item