Organocatalytic, enantioselective synthesis of benzoxaboroles via Wittig/oxa-Michael reaction Cascade of α-formyl boronic acids

Gurupada Hazra; Sanjay Maity; Sudipto Bhowmick; Prasanta Ghorai

doi:10.1039/c6sc04522g

Organocatalytic, enantioselective synthesis of benzoxaboroles via Wittig/oxa-Michael reaction Cascade of α-formyl boronic acids

Gurupada Hazra, Sanjay Maity, Sudipto Bhowmick, Prasanta Ghorai

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37 Scopus citations

Abstract

An unprecedented enantioselective synthesis of 3-substituted benzoxaboroles has been developed. An in situ generated ortho-boronic acid containing chalcone provides the chiral benzoxaboroles via an asymmetric oxa-Michael addition of hydroxyl group attached to the boronic acid triggered by the cinchona alkaloid based chiral amino-squaramide catalysts. In general, good yields with good to excellent enantioselectivities (up to 99%) were obtained. The resulting benzoxaboroles were converted to the corresponding chiral β-hydroxy ketones without affecting the enantioselectivity.

Original language	English (US)
Pages (from-to)	3026-3030
Number of pages	5
Journal	Chemical Science
Volume	8
Issue number	4
DOIs	https://doi.org/10.1039/c6sc04522g
State	Published - 2017
Externally published	Yes

Bibliographical note

Funding Information:
This work has been funded by IISER Bhopal. GH and SM thank CSIR and UGC, New Delhi, India, respectively, for the doctoral fellowship. We are thankful to Dr Deepak Chopra, Associate Professor, IISER Bhopal for his useful suggestions. We are grateful to Mr Lalit M. Jha (IISER Bhopal) for X-ray crystallography.

Publisher Copyright:
© The Royal Society of Chemistry.

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title = "Organocatalytic, enantioselective synthesis of benzoxaboroles via Wittig/oxa-Michael reaction Cascade of α-formyl boronic acids",

abstract = "An unprecedented enantioselective synthesis of 3-substituted benzoxaboroles has been developed. An in situ generated ortho-boronic acid containing chalcone provides the chiral benzoxaboroles via an asymmetric oxa-Michael addition of hydroxyl group attached to the boronic acid triggered by the cinchona alkaloid based chiral amino-squaramide catalysts. In general, good yields with good to excellent enantioselectivities (up to 99%) were obtained. The resulting benzoxaboroles were converted to the corresponding chiral β-hydroxy ketones without affecting the enantioselectivity.",

author = "Gurupada Hazra and Sanjay Maity and Sudipto Bhowmick and Prasanta Ghorai",

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AU - Hazra, Gurupada

AU - Maity, Sanjay

AU - Bhowmick, Sudipto

AU - Ghorai, Prasanta

N1 - Funding Information: This work has been funded by IISER Bhopal. GH and SM thank CSIR and UGC, New Delhi, India, respectively, for the doctoral fellowship. We are thankful to Dr Deepak Chopra, Associate Professor, IISER Bhopal for his useful suggestions. We are grateful to Mr Lalit M. Jha (IISER Bhopal) for X-ray crystallography. Publisher Copyright: © The Royal Society of Chemistry.

PY - 2017

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N2 - An unprecedented enantioselective synthesis of 3-substituted benzoxaboroles has been developed. An in situ generated ortho-boronic acid containing chalcone provides the chiral benzoxaboroles via an asymmetric oxa-Michael addition of hydroxyl group attached to the boronic acid triggered by the cinchona alkaloid based chiral amino-squaramide catalysts. In general, good yields with good to excellent enantioselectivities (up to 99%) were obtained. The resulting benzoxaboroles were converted to the corresponding chiral β-hydroxy ketones without affecting the enantioselectivity.

AB - An unprecedented enantioselective synthesis of 3-substituted benzoxaboroles has been developed. An in situ generated ortho-boronic acid containing chalcone provides the chiral benzoxaboroles via an asymmetric oxa-Michael addition of hydroxyl group attached to the boronic acid triggered by the cinchona alkaloid based chiral amino-squaramide catalysts. In general, good yields with good to excellent enantioselectivities (up to 99%) were obtained. The resulting benzoxaboroles were converted to the corresponding chiral β-hydroxy ketones without affecting the enantioselectivity.

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Organocatalytic, enantioselective synthesis of benzoxaboroles via Wittig/oxa-Michael reaction Cascade of α-formyl boronic acids

Abstract

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