Catalytic Biomimetic Asymmetric Reduction of Alkenes and Imines Enabled by Chiral and Regenerable NAD(P)H Models.
alkenes
asymmetric synthesis
biomimetic chemistry
reduction
synthetic methods
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
04 02 2019
04 02 2019
Historique:
received:
23
11
2018
pubmed:
18
12
2018
medline:
19
8
2020
entrez:
18
12
2018
Statut:
ppublish
Résumé
The development of biomimetic chemistry based on the NAD(P)H with hydrogen gas as terminal reductant is a long-standing challenge. Through rational design of the chiral and regenerable NAD(P)H analogues based on planar-chiral ferrocene, a biomimetic asymmetric reduction has been realized using bench-stable Lewis acids as transfer catalysts. A broad set of alkenes and imines could be reduced with up to 98 % yield and 98 % ee, likely enabled by enzyme-like cooperative bifunctional activation. This reaction represents the first general biomimetic asymmetric reduction (BMAR) process enabled by chiral and regenerable NAD(P)H analogues. This concept demonstrates catalytic utility of a chiral coenzyme NAD(P)H in asymmetric catalysis.
Identifiants
pubmed: 30556234
doi: 10.1002/anie.201813400
doi:
Substances chimiques
Alkenes
0
Imines
0
NADP
53-59-8
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
1813-1817Subventions
Organisme : National Natural Science Foundation of China
ID : 21532006, 21690074
Pays : International
Organisme : Chinese Academy of Sciences
ID : XDB17020300, QYZDJ-SSW-SLH035
Pays : International
Organisme : Dalian Institute of Chemical Physics
ID : DMTO201501
Pays : International
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.