Copper-Free Asymmetric Allylic Alkylation of Trisubstituted Cyclic Allyl Bromides Using Grignard Reagents

Grassi, David; Alexakis, Alexandre

doi:10.1002/anie.201307591

Scientific article

English

Copper-Free Asymmetric Allylic Alkylation of Trisubstituted Cyclic Allyl Bromides Using Grignard Reagents

ContributorsGrassi, David; Alexakis, Alexandre

Published inAngewandte Chemie. International edition in English, vol. 52, no. 51, p. 13642-13646

Publication date2013

Abstract

AAA: The asymmetric allylic alkylation (AAA) of trisubstituted cyclic allyl bromides with Grignard reagents is catalytic (2 mol % of ligand) and regioselective (SN2'/SN2=91:9→100:0). The quaternary carbon centers are formed with good to high enantioselectivity (e.r.=81.5:19.5→96:4).

Keywords

Quaternary stereocenters
Allyl bromides
Asymmetric catalysis
Diaminocarbenes
Grignard reaction

Affiliation entities

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

Research groups

Groupe Alexakis

Citation (ISO format)

GRASSI, David, ALEXAKIS, Alexandre. Copper-Free Asymmetric Allylic Alkylation of Trisubstituted Cyclic Allyl Bromides Using Grignard Reagents. In: Angewandte Chemie. International edition in English, 2013, vol. 52, n° 51, p. 13642–13646. doi: 10.1002/anie.201307591

Article (Published version)

Identifiers

PID : unige:32651
DOI : 10.1002/anie.201307591

Journal ISSN0570-0833

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Creation18/12/2013 09:21:00

First validation18/12/2013 09:21:00

Update time14/03/2023 20:46:43

Status update14/03/2023 20:46:43

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Copper-Free Asymmetric Allylic Alkylation of Trisubstituted Cyclic Allyl Bromides Using Grignard Reagents

AAA: The asymmetric allylic alkylation (AAA) of trisubstituted cyclic allyl bromides with Grignard reagents is catalytic (2 mol % of ligand) and regioselective (SN2'/SN2=91:9→100:0). The quaternary carbon centers are formed with good to high enantioselectivity (e.r.=81.5:19.5→96:4).

Technical informations