Stereoselective Direct Chlorination of Alkenyl MIDA Boronates: Divergent Synthesis of E and Z alpha-Chloroalkenyl Boronates
Stereoselective Direct Chlorination of Alkenyl MIDA Boronates: Divergent Synthesis of E and Z alpha-Chloroalkenyl Boronates
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烯基 MIDA 硼酸酯的立体选择性直接氯化：E 和 Z α-氯烯基硼酸酯的不同合成
DOI：
10.1002/anie.201709070
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发表时间：
2017
期刊：
影响因子：
--
通讯作者：
Wang Honggen
中科院分区：
文献类型：
--
作者：
Zeng Yao-Fu;Ji Wei-Wei;Lv Wen-Xin;Chen Yunyun;Tan Dong-Hang;Li Qingjiang;Wang Honggen
α-氯烯基硼酸酯的单个分子包含亲电 C−Cl 键和亲核 C−B 键，这使它们成为有趣的有机合成子。本文报道了分别使用 tBuOCl 和 PhSeCl 试剂通过烯基 MIDA 硼酸酯直接氯化来立体发散合成 E 和 Zα-氯烯基 N-甲基亚氨基二乙酰 (MIDA) 硼酸酯。两种反应过程都是立体定向的，sp3-B MIDA 硼酸酯的使用是反应活性的关键因素。硼酸盐产品的合成价值也得到了证明。
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 bothEandZα‐chloroalkenylN‐methyliminodiacetyl (MIDA) boronates through the direct chlorination of alkenyl MIDA boronates usingtBuOCl 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.