Synthesis of seven-membered lactones by regioselective and stereoselective iodolactonization of electron-deficient olefins.

Chem Commun (Camb)

Hubei Collaborative Innovation Center for Advanced Chemical Materials, Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, and College of Chemistry and Chemical Engineering, Hubei University, Wuhan, 430062, China. and Department Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, 541004, China.

Published: June 2020

A regio- and stereoselective iodolactonization of internal electron-deficient olefinic acids has been reported, which provides a straightforward access to a series of multi-functionalized seven-membered lactones containing two consecutive chiral centers. The ester substituents on the olefins played a key role in achieving high regioselectivity. This result was proved through experiments and DFT calculations.

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Source
http://dx.doi.org/10.1039/c9cc10080fDOI Listing

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