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- Title
Stepwise Asymmetric Allylic Substitution‐Isomerization Enabled Mimetic Synthesis of Axially Chiral B,N‐Heterocycles.
- Authors
Zhang, Xiu‐Lian; Gu, Jun; Cui, Wen‐Hao; Ye, Zhiwen; Yi, Wenbin; Zhang, Qiang; He, Ying
- Abstract
Axially chiral molecules bearing multiple stereogenic axes are of great importance in the field of organic chemistry. However, the efficient construction of atropisomers featuring two different types of stereogenic axes has rarely been explored. Herein, we report the novel atroposelective synthesis of configurationally stable axially chiral B,N‐heterocycles. By using stepwise asymmetric allylic substitution‐isomerization (AASI) strategy, diaxially chiral B,N‐heterocycles bearing B−C and C−N axes that are related to the moieties of axially chiral enamines and arylborons were also obtained. In this case, all four stereoisomers of diaxially chiral B,N‐heterocycles were stereodivergently afforded in high enantioselectivities. Density functional theory (DFT) studies demonstrated that the NH⋅⋅⋅π interactions played a unique role in the promotion of stereospecific isomerization, thereby leading to the highly efficient central‐to‐axial chirality transfer.
- Subjects
ORGANIC chemistry; DENSITY functional theory; CHIRALITY element; ATROPISOMERS; STEREOISOMERS; ASYMMETRIC synthesis
- Publication
Angewandte Chemie, 2022, Vol 134, Issue 51, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202210456