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

Sub Organic Chemistry and Catalysis

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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