Phenyl versus Ethyl Transfer in the Addition of Organozincs to Aldehydes: A Theoretical Study

Jens Rudolph; Torben Rasmussen; Carsten Bolm; Per-Ola Norrby

Phenyl versus Ethyl Transfer in the Addition of Organozincs to Aldehydes: A Theoretical Study

Jens Rudolph, Torben Rasmussen, Carsten Bolm, Per-Ola Norrby

Department of Chemistry

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

The dramatic improvement in diphenylzinc addition to aldehydes that is obtained by adding diethylzinc was investigated by DFT methods. The strong preference for phenyl over ethyl transfer can be understood in terms of overlap with the phenyl 31 system in the transition state (see picture). Reasons for the high ee value in the presence of Et$-2$/Zn are discussed.

Original language	English
Journal	Angewandte chemie-international edition
Volume	42
Issue number	26
Pages (from-to)	3002-3005
ISSN	1433-7851
Publication status	Published - 2003

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title = "Phenyl versus Ethyl Transfer in the Addition of Organozincs to Aldehydes: A Theoretical Study",

abstract = "The dramatic improvement in diphenylzinc addition to aldehydes that is obtained by adding diethylzinc was investigated by DFT methods. The strong preference for phenyl over ethyl transfer can be understood in terms of overlap with the phenyl 31 system in the transition state (see picture). Reasons for the high ee value in the presence of Et$-2$/Zn are discussed.",

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T1 - Phenyl versus Ethyl Transfer in the Addition of Organozincs to Aldehydes: A Theoretical Study

AU - Rudolph, Jens

AU - Rasmussen, Torben

AU - Bolm, Carsten

AU - Norrby, Per-Ola

PY - 2003

Y1 - 2003

N2 - The dramatic improvement in diphenylzinc addition to aldehydes that is obtained by adding diethylzinc was investigated by DFT methods. The strong preference for phenyl over ethyl transfer can be understood in terms of overlap with the phenyl 31 system in the transition state (see picture). Reasons for the high ee value in the presence of Et$-2$/Zn are discussed.

AB - The dramatic improvement in diphenylzinc addition to aldehydes that is obtained by adding diethylzinc was investigated by DFT methods. The strong preference for phenyl over ethyl transfer can be understood in terms of overlap with the phenyl 31 system in the transition state (see picture). Reasons for the high ee value in the presence of Et$-2$/Zn are discussed.

M3 - Journal article

VL - 42

SP - 3002

EP - 3005

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

SN - 1433-7851

IS - 26

ER -

Phenyl versus Ethyl Transfer in the Addition of Organozincs to Aldehydes: A Theoretical Study

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