Application of N,S-chelating chiral zinc bis(arenethiolate) complexes as new precursor catalysts in the enantioselective addition of diethylzinc to aldehydes

Evelien Rijnberg; Johann T. B. H. Jastrzebski; Maurits D. Janssen; Jaap Boersma; Gerard Van Koten

doi:10.1016/S0040-4039(00)78262-1

Application of N,S-chelating chiral zinc bis(arenethiolate) complexes as new precursor catalysts in the enantioselective addition of diethylzinc to aldehydes

Evelien Rijnberg, Johann T. B. H. Jastrzebski, Maurits D. Janssen, Jaap Boersma, Gerard Van Koten

Utrecht University

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

Abstract

The addition of diethylzinc to aldehydes in the presence of a catalytic amount of enantiomerically pure N,S-chelated bis{2-[(R)-1- (dimethylamino)ethyl]phenylthiolato}zinc, afforded the corresponding secondary alcohols in nearly quantitative yields with optical purities of up to 99% e.e. under mild reaction conditions.

Original language	English
Pages (from-to)	6521-6524
Number of pages	4
Journal	Tetrahedron Letters
Volume	35
Issue number	35
DOIs	https://doi.org/10.1016/S0040-4039(00)78262-1
Publication status	Published - 12 Mar 1994

Keywords

aldehyde derivative
chelating agent
polycyclic aromatic hydrocarbon derivative
zinc derivative
article
chelation
chemical modification
chemical reaction
enantiomer
organic chemistry
stereochemistry

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10.1016/S0040-4039(00)78262-1

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@article{14a83b497855493dad0358dffacd4988,

title = "Application of N,S-chelating chiral zinc bis(arenethiolate) complexes as new precursor catalysts in the enantioselective addition of diethylzinc to aldehydes",

abstract = "The addition of diethylzinc to aldehydes in the presence of a catalytic amount of enantiomerically pure N,S-chelated bis{2-[(R)-1- (dimethylamino)ethyl]phenylthiolato}zinc, afforded the corresponding secondary alcohols in nearly quantitative yields with optical purities of up to 99% e.e. under mild reaction conditions.",

keywords = "aldehyde derivative, chelating agent, polycyclic aromatic hydrocarbon derivative, zinc derivative, article, chelation, chemical modification, chemical reaction, enantiomer, organic chemistry, stereochemistry",

author = "Evelien Rijnberg and Jastrzebski, {Johann T. B. H.} and Janssen, {Maurits D.} and Jaap Boersma and {Van Koten}, Gerard",

year = "1994",

month = mar,

day = "12",

doi = "10.1016/S0040-4039(00)78262-1",

language = "English",

volume = "35",

pages = "6521--6524",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "35",

}

Application of N,S-chelating chiral zinc bis(arenethiolate) complexes as new precursor catalysts in the enantioselective addition of diethylzinc to aldehydes. / Rijnberg, Evelien; Jastrzebski, Johann T. B. H.; Janssen, Maurits D. et al.
In: Tetrahedron Letters, Vol. 35, No. 35, 12.03.1994, p. 6521-6524.

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

TY - JOUR

T1 - Application of N,S-chelating chiral zinc bis(arenethiolate) complexes as new precursor catalysts in the enantioselective addition of diethylzinc to aldehydes

AU - Rijnberg, Evelien

AU - Jastrzebski, Johann T. B. H.

AU - Janssen, Maurits D.

AU - Boersma, Jaap

AU - Van Koten, Gerard

PY - 1994/3/12

Y1 - 1994/3/12

N2 - The addition of diethylzinc to aldehydes in the presence of a catalytic amount of enantiomerically pure N,S-chelated bis{2-[(R)-1- (dimethylamino)ethyl]phenylthiolato}zinc, afforded the corresponding secondary alcohols in nearly quantitative yields with optical purities of up to 99% e.e. under mild reaction conditions.

AB - The addition of diethylzinc to aldehydes in the presence of a catalytic amount of enantiomerically pure N,S-chelated bis{2-[(R)-1- (dimethylamino)ethyl]phenylthiolato}zinc, afforded the corresponding secondary alcohols in nearly quantitative yields with optical purities of up to 99% e.e. under mild reaction conditions.

KW - aldehyde derivative

KW - chelating agent

KW - polycyclic aromatic hydrocarbon derivative

KW - zinc derivative

KW - article

KW - chelation

KW - chemical modification

KW - chemical reaction

KW - enantiomer

KW - organic chemistry

KW - stereochemistry

U2 - 10.1016/S0040-4039(00)78262-1

DO - 10.1016/S0040-4039(00)78262-1

M3 - Article

SN - 0040-4039

VL - 35

SP - 6521

EP - 6524

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 35

ER -

Application of N,S-chelating chiral zinc bis(arenethiolate) complexes as new precursor catalysts in the enantioselective addition of diethylzinc to aldehydes

Abstract

Keywords

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