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Stereoselective Direct Chlorination of Alkenyl MIDA Boronates: Divergent Synthesis of E and Z α‐Chloroalkenyl Boronates
Author(s) -
Zeng YaoFu,
Ji WeiWei,
Lv WenXin,
Chen Yunyun,
Tan DongHang,
Li Qingjiang,
Wang Honggen
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201709070
Subject(s) - synthon , chemistry , stereospecificity , electrophile , reagent , nucleophile , stereoselectivity , reactivity (psychology) , organic synthesis , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
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 t BuOCl and PhSeCl reagents, respectively. Both reaction processes are stereospecific and the use of sp 3 ‐B MIDA boronate is the key contributor to the reactivity. The synthetic value of the boronate products was also demonstrated.