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- Title
Ir‐Catalyzed Enantioselective Synthesis of gem‐Diborylalkenes Enabled by 1,2‐Boron Shift.
- Authors
Ge, Jian‐Fei; Zou, Xi‐Zhang; Liu, Xin‐Ru; Ji, Chong‐Lei; Zhu, Xin‐Yuan; Gao, De‐Wei
- Abstract
Asymmetric cross‐couplings based on 1,2‐carbon migration from B‐ate complexes have been developed efficiently to access valuable organoboronates. However, enantioselective reactions triggered by 1,2‐boron shift have remained to be unaddressed synthetic challenge. Here, Ir‐catalyzed asymmetric allylic alkylation enabled by 1,2‐boron shift was developed. In this reaction, we disclosed that excellent enantioselectivities were achieved through an interesting dynamic kinetic resolution (DKR) process of allylic carbonates at the elevated temperature. Notably, the highly valuable (bis‐boryl)alkenes have enabled an array of diversifications to access versatile molecules. Extensive experimental and computational studies were conducted to elucidate the reaction mechanism of DKR process and clarify the origin of excellent enantioselectivities.
- Subjects
KINETIC resolution; ALLYLIC amination; ALLYLIC alkylation; HIGH temperatures; ALKENES
- Publication
Angewandte Chemie, 2023, Vol 135, Issue 32, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202307447