Copper(I) thiolate catalysts in asymmetric conjugate addition reactions

Anne M. Arink; Thijs W. Braam; Roy Keeris; Johann T. B. H. Jastrzebski; Cyril Benhaim; Stéphane Rosset; Alexandre Alexakis; Gerard Van Koten

Copper(I) thiolate catalysts in asymmetric conjugate addition reactions

Anne M. Arink
, Thijs W. Braam
, Roy Keeris
, Johann T. B. H. Jastrzebski
, Cyril Benhaim
, Stéphane Rosset
, Alexandre Alexakis
, Gerard Van Koten

Sub Organic Chemistry and Catalysis

Utrecht University
External unknown

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

Abstract

Equation presented. Full conversion and enantioselectivities up to 83% have been obtained in the conjugate addition reactions of diethyl zinc to Michael acceptors catalyzed by well-defined (chiral) copper(I) aminoarenethiolates. Interesting differences between organozinc or Grignard reagents have been found: for cyclic enones R2Zn reagents afford better results, whereas earlier work showed that RMgX reagents react more selectively with acyclic enones.

Original language	English
Pages (from-to)	1959-1962
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	12
Publication status	Published - 10 Jun 2004

Keywords

copper complex
ketone derivative
reagent
thiol derivative
zinc
addition reaction
article
catalysis
catalyst
chemical reaction
conjugate
enantioselectivity
Grignard reaction
Michael addition
reaction analysis

Cite this

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title = "Copper(I) thiolate catalysts in asymmetric conjugate addition reactions",

abstract = "Equation presented. Full conversion and enantioselectivities up to 83\% have been obtained in the conjugate addition reactions of diethyl zinc to Michael acceptors catalyzed by well-defined (chiral) copper(I) aminoarenethiolates. Interesting differences between organozinc or Grignard reagents have been found: for cyclic enones R2Zn reagents afford better results, whereas earlier work showed that RMgX reagents react more selectively with acyclic enones.",

keywords = "copper complex, ketone derivative, reagent, thiol derivative, zinc, addition reaction, article, catalysis, catalyst, chemical reaction, conjugate, enantioselectivity, Grignard reaction, Michael addition, reaction analysis",

author = "Arink, \{Anne M.\} and Braam, \{Thijs W.\} and Roy Keeris and Jastrzebski, \{Johann T. B. H.\} and Cyril Benhaim and St{\'e}phane Rosset and Alexandre Alexakis and \{Van Koten\}, Gerard",

year = "2004",

month = jun,

day = "10",

language = "English",

volume = "6",

pages = "1959--1962",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Copper(I) thiolate catalysts in asymmetric conjugate addition reactions

AU - Arink, Anne M.

AU - Braam, Thijs W.

AU - Keeris, Roy

AU - Jastrzebski, Johann T. B. H.

AU - Benhaim, Cyril

AU - Rosset, Stéphane

AU - Alexakis, Alexandre

AU - Van Koten, Gerard

PY - 2004/6/10

Y1 - 2004/6/10

N2 - Equation presented. Full conversion and enantioselectivities up to 83% have been obtained in the conjugate addition reactions of diethyl zinc to Michael acceptors catalyzed by well-defined (chiral) copper(I) aminoarenethiolates. Interesting differences between organozinc or Grignard reagents have been found: for cyclic enones R2Zn reagents afford better results, whereas earlier work showed that RMgX reagents react more selectively with acyclic enones.

AB - Equation presented. Full conversion and enantioselectivities up to 83% have been obtained in the conjugate addition reactions of diethyl zinc to Michael acceptors catalyzed by well-defined (chiral) copper(I) aminoarenethiolates. Interesting differences between organozinc or Grignard reagents have been found: for cyclic enones R2Zn reagents afford better results, whereas earlier work showed that RMgX reagents react more selectively with acyclic enones.

KW - copper complex

KW - ketone derivative

KW - reagent

KW - thiol derivative

KW - zinc

KW - addition reaction

KW - article

KW - catalysis

KW - catalyst

KW - chemical reaction

KW - conjugate

KW - enantioselectivity

KW - Grignard reaction

KW - Michael addition

KW - reaction analysis

M3 - Article

SN - 1523-7060

VL - 6

SP - 1959

EP - 1962

JO - Organic Letters

JF - Organic Letters

IS - 12

ER -

Copper(I) thiolate catalysts in asymmetric conjugate addition reactions

Abstract

Keywords

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