Electronically Activated Organoboron Catalysts for Enantioselective Propargyl Addition to Trifluoromethyl Ketones | Zendy

Mszar Nicholas W. | Zendy; Mikus Malte S. | Zendy; Torker Sebastian | Zendy; Haeffner Fredrik | Zendy; Hoveyda Amir H. | Zendy

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Electronically Activated Organoboron Catalysts for Enantioselective Propargyl Addition to Trifluoromethyl Ketones

Author(s) -

Mszar Nicholas W.,

Mikus Malte S.,

Torker Sebastian,

Haeffner Fredrik,

Hoveyda Amir H.

Publication year - 2017

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201703844

Subject(s) - enantioselective synthesis , trifluoromethyl , propargyl , chemistry , moiety , aryl , catalysis , silylation , yield (engineering) , alkyl , organic chemistry , combinatorial chemistry , materials science , metallurgy

A broadly applicable, practical, scalable, efficient and highly α‐ and enantioselective method for addition of a silyl‐protected propargyl moiety to trifluoromethyl ketones has been developed. Reactions, promoted by 2.0 mol % of a catalyst that is derived in situ from a readily accessible aminophenol compound at ambient temperature, were complete after only 15 minutes at room temperature. The desired tertiary alcohols were isolated in up to 97 % yield and 98.5:1.5 enantiomeric ratio. Alkyl‐, alkenyl‐, alkynyl‐, aryl‐ or heteroaryl‐substituted trifluoromethyl ketones can be used. Utility is highlighted by application to a transformation that is relevant to enantioselective synthesis of BI 653048, a compound active against rheumatoid arthritis.

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