Catalytic asymmetric conjugate addition on macrocyclic and acyclic enones. Synthesis of R-(-)-Muscone

Alexakis, Alexandre; Benhaim, Cyril; Fournioux, Xavier; van den Heuvel, Alexandra; Leveque, Jean-Marc; March, Sebastien; Rosset, Stéphane

doi:10.1055/s-1999-2931

Scientific article

English

Catalytic asymmetric conjugate addition on macrocyclic and acyclic enones. Synthesis of R-(-)-Muscone

Contributors

Alexakis, Alexandre; Benhaim, Cyril; Fournioux, Xavier; van den Heuvel, Alexandra; Leveque, Jean-Marc; March, Sebastien; Rosset, Stéphane

Published in

Synlett, no. 11, p. 1811-1813

Publication date

1999

Abstract

The asymmetric conjugate addition of diethyl zinc to acyclic enones is described. With 1% Cu(OTf)2 and 2% of a chiral phosphite ligand, the catalyst allowed ee's up to 92'% to be obtained. The addition of dimethyl zinc to a macrocyclic 15-membered ring enone lead to optically active R-(-)-muscone, in 53% yield and 79% enantiomeric excess.

Keywords

Conjugate addition
Catalysis
Copper
Asymmetry
Dialkyl zinc
Muscone

UNIGE affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

ALEXAKIS, Alexandre et al. Catalytic asymmetric conjugate addition on macrocyclic and acyclic enones. Synthesis of R-(-)-Muscone. In: Synlett, 1999, n° 11, p. 1811–1813. doi: 10.1055/s-1999-2931

Article (Published version)

Identifiers

PID : unige:8157
DOI : 10.1055/s-1999-2931

Journal ISSN

0936-5214

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21/06/2010 14:44:20

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Update

14/03/2023 15:48:21

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14/03/2023 15:48:21

Last indexation

29/10/2024 15:33:59

Catalytic asymmetric conjugate addition on macrocyclic and acyclic enones. Synthesis of R-(-)-Muscone

Contributors

Published in

Publication date

Abstract

Keywords

UNIGE affiliation entities

Citation (ISO format)

Main files (1)

Identifiers

Journal ISSN

Technical informations

Creation

First validation

Update

Status update

Last indexation