Catalytic Enantioselective Protonation/Nucleophilic Addition of Diazoesters with Chiral Oxazaborolidinium Ion Activated Carboxylic Acids

A new chiral Brønsted acid derived from carboxylic acid and a chiral oxazaborolidinium ion (COBI), as an activator, is introduced. This acid was successfully applied as a catalyst for the highly enantioselective protonation/nucleophilic addition of diazoesters with carboxylic acids. COBI‐Wan: A new...

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie International Edition 2017-03, Vol.56 (14), p.3977-3981
Main Authors: Kang, Ki‐Tae, Kim, Seung Tae, Hwang, Geum‐Sook, Ryu, Do Hyun
Format: Article
Language:English
Subjects:
asymmetric catalysis
boron
Brønsted acid
Carboxylic acids
diazo compounds
Enantiomers
Protonation
reaction mechanisms
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:A new chiral Brønsted acid derived from carboxylic acid and a chiral oxazaborolidinium ion (COBI), as an activator, is introduced. This acid was successfully applied as a catalyst for the highly enantioselective protonation/nucleophilic addition of diazoesters with carboxylic acids. COBI‐Wan: A new chiral Brønsted acid derived from a carboxylic acid and a chiral oxazaborolidinium ion (COBI), as an activator, is introduced. This acid was successfully applied as a catalyst for the highly enantioselective protonation/nucleophilic addition of diazoesters and carboxylic acids. Tf=trifluoromethanesulfonyl.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201612655