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CF Bond Activation of Unactivated Aliphatic Fluorides: Synthesis of Fluoromethyl‐3,5‐diaryl‐2‐oxazolidinones by Desymmetrization of 2‐Aryl‐1,3‐difluoropropan‐2‐ols
Author(s) -
Haufe Günter,
Suzuki Satoru,
Yasui Hiroyuki,
Terada Chisato,
Kitayama Takashi,
Shiro Motoo,
Shibata Norio
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201207304
Subject(s) - desymmetrization , aryl , chemistry , trimethylsilyl , bond cleavage , difluoride , acetamide , catalysis , organic chemistry , combinatorial chemistry , medicinal chemistry , enantioselective synthesis , alkyl
How to lose fluorine : Biologically relevant oxazolidinones 1 were synthesized through the desymmetrization of unactivated aliphatic difluorides by Si‐induced catalytic CF bond‐cleavage using BSA/CsF (BSA=bis(trimethylsilyl)acetamide). The direct transformation of 2 with isocyanates into 1 by cascade carbamoylation/cyclization, in which cyclization is induced by Na‐assisted CF bond activation, was also achieved.