Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
4 years ago

Stereoselective Direct Chlorination of Alkenyl MIDA Boronates: Divergent Synthesis of E and Z α-Chloroalkenyl Boronates

Stereoselective Direct Chlorination of Alkenyl MIDA Boronates: Divergent Synthesis of E and Z α-Chloroalkenyl Boronates
Qingjiang Li, Yao-Fu Zeng, Wen-Xin Lv, Yunyun Chen, Honggen Wang, Wei-Wei Ji, Dong-Hang Tan
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. One Way or Another: Stereodivergent syntheses of both E and Z α-chloroalkenyl N-methyliminodiacetyl (MIDA) boronates were achieved through the direct chlorination of E-alkenyl MIDA boronates using tBuOCl and PhSeCl reagents, respectively. Both reaction processes are stereospecific and the sp3-B MIDA boronate plays the key role to the reactivity. Broad substrate scope was observed and the synthetic value of the boronate products was demonstrated.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201709070

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