Manifestation of Felkin-Anh control in enantioselective acyl transfer catalysis: Kinetic resolution of carboxylic acids

Xing Yang; Peng Liu; K. N. Houk; Vladimir B. Birman

doi:10.1002/anie.201203327

Manifestation of Felkin-Anh control in enantioselective acyl transfer catalysis: Kinetic resolution of carboxylic acids

Xing Yang
, Peng Liu
, K. N. Houk
, Vladimir B. Birman

Department of Chemistry

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

37 Scopus citations

Abstract

Under control: The classical polar Felkin-Anh model has been applied for the first time to the analysis of diastereoselectivity in acylation reactions (see scheme). Computational studies demonstrate that stereoelectronic effects control the enantioselectivity in asymmetric catalytic alcoholysis of acyclic anhydrides.

Original language	English
Pages (from-to)	9638-9642
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	51
Issue number	38
DOIs	https://doi.org/10.1002/anie.201203327
State	Published - Sep 17 2012

Keywords

asymmetric organocatalysis
enantioselective alcoholysis
Felkin-Anh Model
kinetic resolution
stereoelectronic control

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10.1002/anie.201203327

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title = "Manifestation of Felkin-Anh control in enantioselective acyl transfer catalysis: Kinetic resolution of carboxylic acids",

abstract = "Under control: The classical polar Felkin-Anh model has been applied for the first time to the analysis of diastereoselectivity in acylation reactions (see scheme). Computational studies demonstrate that stereoelectronic effects control the enantioselectivity in asymmetric catalytic alcoholysis of acyclic anhydrides.",

keywords = "asymmetric organocatalysis, enantioselective alcoholysis, Felkin-Anh Model, kinetic resolution, stereoelectronic control",

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journal = "Angewandte Chemie - International Edition",

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T2 - Kinetic resolution of carboxylic acids

AU - Yang, Xing

AU - Liu, Peng

AU - Houk, K. N.

AU - Birman, Vladimir B.

PY - 2012/9/17

Y1 - 2012/9/17

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AB - Under control: The classical polar Felkin-Anh model has been applied for the first time to the analysis of diastereoselectivity in acylation reactions (see scheme). Computational studies demonstrate that stereoelectronic effects control the enantioselectivity in asymmetric catalytic alcoholysis of acyclic anhydrides.

KW - asymmetric organocatalysis

KW - enantioselective alcoholysis

KW - Felkin-Anh Model

KW - kinetic resolution

KW - stereoelectronic control

UR - https://www.scopus.com/pages/publications/84866391660

U2 - 10.1002/anie.201203327

DO - 10.1002/anie.201203327

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SN - 1433-7851

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 38

ER -

Manifestation of Felkin-Anh control in enantioselective acyl transfer catalysis: Kinetic resolution of carboxylic acids

Abstract

Keywords

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