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- Title
Synthesis of Axially Chiral Styrenes through Pd‐Catalyzed Asymmetric C−H Olefination Enabled by an Amino Amide Transient Directing Group.
- Authors
Song, Hong; Li, Ya; Yao, Qi‐Jun; Jin, Liang; Liu, Lei; Liu, Yan‐Hua; Shi, Bing‐Feng
- Abstract
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 PdII‐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 CoIII‐catalyzed enantioselective C(sp3)−H amidation of thioamide. Mechanistic studies suggest that C−H cleavage is the enantioselectivity‐determining step.
- Subjects
STYRENE; CARBOXYLIC acid derivatives
- Publication
Angewandte Chemie, 2020, Vol 132, Issue 16, p6638
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201915949