Nickel-Catalyzed Double Bond Transposition of Alkenyl Boronates for in Situ syn-Selective Allylboration Reactions.
Nickel-Catalyzed Double Bond Transposition of Alkenyl Boronates for in Situ syn-Selective Allylboration Reactions.
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DOI：
10.1021/acs.orglett.5b03585
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发表时间：
2016-01
期刊：
影响因子：
5.2
通讯作者：
F. Weber;Monika Ballmann;Corinna Kohlmeyer;G. Hilt
中科院分区：
文献类型：
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作者：
F. Weber;Monika Ballmann;Corinna Kohlmeyer;G. Hilt
采用NiCl2（dppp）、锌粉、ZnI2和Ph2PH组成的高活性镍-催化剂体系，实现了纯烯丙基品萘醇硼酯的转位反应。原位生成的z -丁基蒎烯醇硼酯与多种醛反应生成具有高非对映选择性的同构丙烯醇。目前的镍催化反应与村上报道的铱催化转位反应相辅相成，从而产生相应的反同丙烯醇。同时，还实现了戊烯醇硼酯的多次转位反应。
The transposition of a homoallyl pinacol boronic ester was realized by a highly reactive nickel-catalyst system comprising NiCl2(dppp), zinc powder, ZnI2, and Ph2PH. The in situ generated Z-crotyl pinacol boronic esters were reacted with various aldehydes to form syn-homoallylic alcohols in high diastereoselectivities. The present nickel-catalyzed reaction is complementary to the iridium-catalyzed transposition reported by Murakami leading to the corresponding anti-homoallylic alcohols. Also, the multiple transposition of pentenyl pinacol boronic ester was realized.