Synthesis of Enantioenriched β‑Hydroxy-γ-Acetal Enamides by Rhodium-Catalyzed Asymmetric Transfer Hydrogenation

Synthesis of Enantioenriched β‑Hydroxy-γ-Acetal Enamides by Rhodium-Catalyzed Asymmetric Transfer Hydrogenation

The asymmetric reduction of β-keto-γ-acetal enamides has been investigated. A wide range of enantioenriched β-hydroxy-γ-acetal enamides were obtained through asymmetric transfer hydrogenation catalyzed by a tethered Rh­(III)-DPEN complex with yields up to quantitative and enantioselectivities up to...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters Vol. 22; no. 10; pp. 3911 - 3914
Main Authors: Westermeyer, Anne, Guillamot, Gérard, Phansavath, Phannarath, Ratovelomanana-Vidal, Virginie
Format: Journal Article
Language:English
Published: United States American Chemical Society 15-05-2020
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The asymmetric reduction of β-keto-γ-acetal enamides has been investigated. A wide range of enantioenriched β-hydroxy-γ-acetal enamides were obtained through asymmetric transfer hydrogenation catalyzed by a tethered Rh­(III)-DPEN complex with yields up to quantitative and enantioselectivities up to 99%. The reaction proved to be highly chemoselective toward the reduction of the carbonyl group over the CC bond.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c01193