Copper-Catalyzed Enantioselective Conjugate Addition to α,β-Unsaturated Aldehydes with Various Organometallic Reagents

Contal, Sylvie; Gremaud, Ludovic; Palais, Laetitia; Babel, Lucille; Alexakis, Alexandre

doi:10.1055/s-0035-1562487

Scientific article

English

Copper-Catalyzed Enantioselective Conjugate Addition to α,β-Unsaturated Aldehydes with Various Organometallic Reagents

Contributors

Contal, Sylvie; Gremaud, Ludovic; Palais, Laetitia; Babel, Lucille; Alexakis, Alexandre

Published in

Synthesis, vol. 48, no. 19, p. 3301-3308

Publication date

2016

Abstract

β-Substituted aldehydes constitute a very important class of compounds found in nature. Synthesis of this motif can be envisioned by C–C bond formation on enals. For this purpose, we report herein the development of enantioselective copper-catalyzed conjugate addition of various organometallic reagents to α,β-unsaturated aldehydes with (R)-H8BINAP, (R)-TolBINAP, and (R)-SEGPHOS as chiral ligands. Three sets of conditions were successfully developed and several enals were used. Reactivity and regio- and enantioselectivities were strongly dependent on reaction conditions and substrates. Good to excellent regio- and enantioselectivities were obtained with zinc reagents R2Zn and aluminum reagents R3Al. However, the asymmetric conjugate addition of Grignard reagents afforded only moderate to good regio- and enantioselectivities.

Keywords

Α,β-unsaturated aldehydes
Conjugate addition
Organometallic reagents
Enantioselectivity
Natural products

UNIGE affiliation entities

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

UNIGE research groups

Groupe Alexakis

Citation (ISO format)

CONTAL, Sylvie et al. Copper-Catalyzed Enantioselective Conjugate Addition to α,β-Unsaturated Aldehydes with Various Organometallic Reagents. In: Synthesis, 2016, vol. 48, n° 19, p. 3301–3308. doi: 10.1055/s-0035-1562487

Article (Published version)

Identifiers

PID : unige:86676
DOI : 10.1055/s-0035-1562487

Journal ISSN

0039-7881

698views

2downloads

Creation

01/09/2016 11:22:00

First validation

01/09/2016 11:22:00

Update

15/03/2023 00:41:25

Status update

15/03/2023 00:41:24

Last indexation

31/10/2024 04:21:58

Copper-Catalyzed Enantioselective Conjugate Addition to α,β-Unsaturated Aldehydes with Various Organometallic Reagents

Contributors

Published in

Publication date

Abstract

Keywords

UNIGE affiliation entities

UNIGE research groups

Citation (ISO format)

Main files (1)

Identifiers

Journal ISSN

Technical informations

Creation

First validation

Update

Status update

Last indexation