Catalytic Asymmetric Conjugate Addition of Carboxylic Acids via Oxa-Michael Reaction of Peroxy Hemiacetals followed by Kornblum DeLaMare Fragmentation

Biswajit Parhi, Sanjay Maity, Prasanta Ghorai

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18 Scopus citations

Abstract

Disclosed herein an overall methodology constitutes an equivalent to the long sought after enantioselective intramolecular oxa-Michael (IOM) reaction of carboxylic acids. An organocatalyzed IOM reaction of in situ formed peroxy hemiacetals followed by a Kornblum DeLaMare type rearrangement cascade provides a broad class of chiral lactones in good yields and with excellent enatioselectvities. Remarkably, the pure chiral lactones are obtained without any silica gel column chromatography, and in many cases, the enantioselectivity is further increased by a simple hexane wash of the isolated solid products.

Original languageEnglish (US)
Pages (from-to)5220-5223
Number of pages4
JournalOrganic Letters
Volume18
Issue number20
DOIs
StatePublished - Oct 21 2016

Bibliographical note

Funding Information:
This work has been supported by CSIR, New Delhi, and IISER Bhopal. B.P. thanks CSIR, New Delhi, and S.M. thanks UGC, New Delhi, India, for fellowships.

Publisher Copyright:
© 2016 American Chemical Society.

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