An α-diaminoboryl carbanion assisted stereoselective single-pot preparation of α,β-disubstituted acrylonitriles.
An α-diaminoboryl carbanion assisted stereoselective single-pot preparation of α,β-disubstituted acrylonitriles.
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DOI：
10.1021/jo201280x
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发表时间：
2011-08
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影响因子：
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通讯作者：
T. Tomioka;Rambabu Sankranti;Trey G. Vaughan;Toshihide Maejima;Takayoshi Yanase
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文献类型：
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作者：
T. Tomioka;Rambabu Sankranti;Trey G. Vaughan;Toshihide Maejima;Takayoshi Yanase
α-二氨基硼基碳负离子介导的一锅烯烃化反应以立体选择性的方式将乙腈或同系物腈直接转化为一系列α，β-二取代丙烯腈。该方案涉及α-取代的α-二氨基硼基乙腈的形成和随后与醛的烯化。使用芳基或共轭醛优先产生（Z）-丙烯腈，而脂肪族醛产生（E）-异构体作为主要产物。两个互补的方法，线性方法和发散方法，开发。
An α-diaminoboryl carbanion-mediated one-pot olefination directly converts an acetonitrile or the homologous nitrile into a series of α,β-disubstituted acrylonitriles in a stereoselective manner. The protocol involves the formation of an α-substituted α-diaminoboryl acetonitrile and subsequent olefination with an aldehyde. The use of an aryl or conjugated aldehyde preferentially leads to a (Z)-acrylonitrile, while an aliphatic aldehyde gave an (E)-isomer as a major product. Two complementary approaches, a linear method and a divergent method, are developed.