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Catalytic Enantioselective Arylation and Heteroarylation of Ketones with Organotitanium Reagents Generated In Situ
Author(s) -
Matsuda Atsushi,
Ushimaru Tomoya,
Kobayashi Yusuke,
Harada Toshiro
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201701395
Subject(s) - enantioselective synthesis , in situ , catalysis , reagent , combinatorial chemistry , chemistry , organic chemistry
A practical and useful, catalytic enantioselective method has been developed for the synthesis of tertiary diaryl and aryl heteroaryl carbinols starting from commercially available aromatic ketones and aryl or heteroaryl bromides. In this method, organotitanium reagents are generated in situ from the bromides by lithiation with n BuLi followed by transmetallation of the resulting organolithiums with ClTi(O i Pr) 3 . Treatment of the ketones with the titanium reagents in the presence of ( R )‐3‐(3,5‐bistrifluoromehthylphenyl)‐1,1′‐bi‐2‐naphthol (BTFP‐BINOL) affords the corresponding tertiary alcohols in high enantioselectivities and yields. The reaction can also start with furan and 2‐thienyllithium. The method is operationally simple and can be conducted on a 10‐mmol scale without any difficulties.