Premium
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
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.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom