CF Bond Activation of Unactivated Aliphatic Fluorides: Synthesis of Fluoromethyl‐3,5‐diaryl‐2‐oxazolidinones by Desymmetrization of 2‐Aryl‐1,3‐difluoropropan‐2‐ols | Zendy

Haufe Günter | Zendy; Suzuki Satoru | Zendy; Yasui Hiroyuki | Zendy; Terada Chisato | Zendy; Kitayama Takashi | Zendy; Shiro Motoo | Zendy; Shibata Norio | Zendy

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CF 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.

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