期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 16, 页码 6576-6580出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201915949
关键词
atroposelectivity; axially chiral styrenes; C-H olefination; palladium; transient directing groups
资金
- NSFC [21772170, 21925109]
- Outstanding Young Talents of Zhejiang Province High-level Personnel of Special Support [ZJWR0108]
- Fundamental Research Funds for the Central Universities [2018XZZX001-02]
- Zhejiang Provincial NSFC [LR17B020001]
The atroposelective synthesis of axially chiral styrenes remains a formidable challenge due to their relatively lower rotational barriers compared to the biaryl atropoisomers. Herein, we describe the construction of axially chiral styrenes through Pd-II-catalyzed atroposelective C-H olefination, using a bulky amino amide as a transient chiral auxiliary. Various axially chiral styrenes were produced with good yields and high enantioselectivity (up to 95 % yield and 99 % ee). Carboxylic acid derivatives of the resulting axially chiral styrenes showed superior enantiocontrol over the biaryl counterparts in Co-III-catalyzed enantioselective C(sp(3))-H amidation of thioamide. Mechanistic studies suggest that C-H cleavage is the enantioselectivity-determining step.
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