Carbene-Catalyzed Dynamic Kinetic Resolution and Asymmetric Acylation of Hydroxyphthalides and Related Natural Products

Yingguo Liu; Pankaj Kumar Majhi; Runjiang Song; Chengli Mou; Lin Hao; Huifang Chai; Zhichao Jin; Yonggui Robin Chi

doi:10.1002/anie.201912926

Carbene-Catalyzed Dynamic Kinetic Resolution and Asymmetric Acylation of Hydroxyphthalides and Related Natural Products

Yingguo Liu, Pankaj Kumar Majhi, Runjiang Song, Chengli Mou, Lin Hao, Huifang Chai^*, Zhichao Jin, Yonggui Robin Chi

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

35 Citations (Scopus)

Abstract

A catalytic dynamic kinetic resolution and asymmetric acylation reaction of hydroxyphthalides is developed. The reaction involves formation of a carbene catalyst derived chiral acyl azolium intermediate that effectively differentiates the two enantiomers of racemic hydroxyphthalides. The method allows quick access to enantiomerically enriched phthalidyl esters with proven applications in medicine. It also enables asymmetric modification of natural products and other functional molecules that contain acetal/ketal groups, such as corollosporine and fimbricalyxlactone C.

Original language	English
Pages (from-to)	3859-3863
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	59
Issue number	10
DOIs	https://doi.org/10.1002/anie.201912926
Publication status	Published - Mar 2 2020
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

chirality
kinetic resolution
N-heterocyclic carbenes
natural products
organocatalysis

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10.1002/anie.201912926

Cite this

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title = "Carbene-Catalyzed Dynamic Kinetic Resolution and Asymmetric Acylation of Hydroxyphthalides and Related Natural Products",

abstract = "A catalytic dynamic kinetic resolution and asymmetric acylation reaction of hydroxyphthalides is developed. The reaction involves formation of a carbene catalyst derived chiral acyl azolium intermediate that effectively differentiates the two enantiomers of racemic hydroxyphthalides. The method allows quick access to enantiomerically enriched phthalidyl esters with proven applications in medicine. It also enables asymmetric modification of natural products and other functional molecules that contain acetal/ketal groups, such as corollosporine and fimbricalyxlactone C.",

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doi = "10.1002/anie.201912926",

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AU - Liu, Yingguo

AU - Majhi, Pankaj Kumar

AU - Song, Runjiang

AU - Mou, Chengli

AU - Hao, Lin

AU - Chai, Huifang

AU - Jin, Zhichao

AU - Chi, Yonggui Robin

PY - 2020/3/2

Y1 - 2020/3/2

N2 - A catalytic dynamic kinetic resolution and asymmetric acylation reaction of hydroxyphthalides is developed. The reaction involves formation of a carbene catalyst derived chiral acyl azolium intermediate that effectively differentiates the two enantiomers of racemic hydroxyphthalides. The method allows quick access to enantiomerically enriched phthalidyl esters with proven applications in medicine. It also enables asymmetric modification of natural products and other functional molecules that contain acetal/ketal groups, such as corollosporine and fimbricalyxlactone C.

AB - A catalytic dynamic kinetic resolution and asymmetric acylation reaction of hydroxyphthalides is developed. The reaction involves formation of a carbene catalyst derived chiral acyl azolium intermediate that effectively differentiates the two enantiomers of racemic hydroxyphthalides. The method allows quick access to enantiomerically enriched phthalidyl esters with proven applications in medicine. It also enables asymmetric modification of natural products and other functional molecules that contain acetal/ketal groups, such as corollosporine and fimbricalyxlactone C.

KW - chirality

KW - kinetic resolution

KW - N-heterocyclic carbenes

KW - natural products

KW - organocatalysis

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Carbene-Catalyzed Dynamic Kinetic Resolution and Asymmetric Acylation of Hydroxyphthalides and Related Natural Products

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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