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- Title
Stereoselective Direct Chlorination of Alkenyl MIDA Boronates: Divergent Synthesis of E and Z α-Chloroalkenyl Boronates.
- Authors
Zeng, Yao ‐ Fu; Ji, Wei ‐ Wei; Lv, Wen ‐ Xin; Chen, Yunyun; Tan, Dong ‐ Hang; Li, Qingjiang; Wang, Honggen
- Abstract
The individual molecules of α-chloroalkenyl boronates include both an electrophilic C−Cl bond and a nucleophilic C−B bond, which makes them intriguing organic synthons. Reported herein is a stereodivergent synthesis of both E and Z α-chloroalkenyl N-methyliminodiacetyl (MIDA) boronates through the direct chlorination of alkenyl MIDA boronates using tBuOCl and PhSeCl reagents, respectively. Both reaction processes are stereospecific and the use of sp3-B MIDA boronate is the key contributor to the reactivity. The synthetic value of the boronate products was also demonstrated.
- Subjects
STEREOSELECTIVE reactions; CHLORINATION; ALKENYL group; BORON; CHEMICAL synthesis; ELECTROPHILES
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 46, p14899
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201709070