Zinc‐Catalyzed Asymmetric Hydrosilylation of Cyclic Imines: Synthesis of Chiral 2‐Aryl‐Substituted Pyrrolidines as Pharmaceutical Building Blocks

The first successful enantioselective hydrosilylation of cyclic imines promoted by a chiral zinc complex is reported. In situ generated zinc‐ProPhenol complex with silane afforded pharmaceutically relevant enantioenriched 2‐aryl‐substituted pyrrolidines in high yields and with excellent enantioselec...

Full description

Saved in:
Bibliographic Details
Published in:Advanced synthesis & catalysis 2021-03, Vol.363 (5), p.1317-1321
Main Authors: Węglarz, Izabela, Michalak, Karol, Mlynarski, Jacek
Format: Article
Language:English
Subjects:
Amines
Aromatic compounds
Asymmetric synthesis
Cyclic imines
Enantiomers
Hydrosilylation
Imines
Pharmaceuticals
Reduction
Substitutes
Zinc
Zinc compounds
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The first successful enantioselective hydrosilylation of cyclic imines promoted by a chiral zinc complex is reported. In situ generated zinc‐ProPhenol complex with silane afforded pharmaceutically relevant enantioenriched 2‐aryl‐substituted pyrrolidines in high yields and with excellent enantioselectivities (up to 99% ee). The synthetic utility of presented methodology is demonstrated in an efficient synthesis of the corresponding chiral cyclic amines, being pharmaceutical drug precursors to the Aticaprant and Larotrectinib.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202001043