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Palladium-Catalyzed Enantioselective Arylation of Racemic Ketones to Form Bridged Bicycles via Dynamic Kinetic Resolution

Authors :
William Ray Jun Jie Oh
Jianrong Steve Zhou
Xiaolei Huang
School of Physical and Mathematical Sciences
Source :
Angewandte Chemie International Edition. 57:7673-7677
Publication Year :
2018
Publisher :
Wiley, 2018.

Abstract

Enantioselective α‐arylation of racemic ketones containing existing α′‐stereocenters is reported for the first time via base‐induced dynamic kinetic resolution. Bridged bicyclic rings are formed in good ee values, which are difficult to obtain otherwise. Furthermore, reactions in DMSO‐d6 resulted in extensive deuteration of both α‐ and α′‐positions in the products, thus supporting a pathway involving rapid, reversible deprotonation of ketones under catalytic conditions. MOE (Min. of Education, S’pore) Accepted version

Details

ISSN :
14337851
Volume :
57
Database :
OpenAIRE
Journal :
Angewandte Chemie International Edition
Accession number :
edsair.doi.dedup.....4e3224470a1c9a9069d84a98be3d0b89
Full Text :
https://doi.org/10.1002/anie.201804318