Palladium Catalyzed Asymmetric Three-Component Coupling of Boronic Esters, Indoles, and Allylic Acetates.

Palladium Catalyzed Asymmetric Three-Component Coupling of Boronic Esters, Indoles, and Allylic Acetates.
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钾酯,吲哚和烯丙基醋酸盐的催化不对称的三成分偶联。

DOI:
10.1021/jacs.7b01410
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发表时间:
2017-05-03
影响因子:
15
通讯作者:
Ready JM
Ready JM
中科院分区:
化学1区
文献类型:
--
作者:
Panda S;Ready JM

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硼酸酯与2-锂化吲哚反应形成硼酸酯中间体。硼酸酯与乙酸烯丙酯在(BINAP)Pd催化剂的存在下反应以烯丙基化C3,同时烷基从吲哚的B迁移到C2。总的来说,该方法是一种三组分偶联,其连接烯丙基乙酸酯、吲哚和有机-B(pin)物质以提供具有高对映体、区域和双立体选择性的取代的吲哚和吲哚啉。
Boronic esters react with 2-lithiated indoles to form boronate intermediates. The boronate reacts with allylic acetates in the presence of (BINAP)Pd catalysts to allylate C3 concurrent with alkyl migration from B to C2 of the indole. Overall, the process is a three-component coupling that joins an allylic acetate, and indole and an organo-B(pin) species to provide substituted indoles and indolines with high enantio-, regio-, and dia-stereo-selectivity.
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