Nucleophilic Addition of Alkanenitriles to Aldehydes via N-Silyl Ketene Imines Generated In Situ
Nucleophilic Addition of Alkanenitriles to Aldehydes via N-Silyl Ketene Imines Generated In Situ
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DOI：
10.1055/s-0036-1588424
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发表时间：
2017-05
期刊：
影响因子：
2
通讯作者：
Fumihiko Yoshimura;Hiroki Saito;Taiki Abe;K. Tanino
中科院分区：
文献类型：
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作者：
Fumihiko Yoshimura;Hiroki Saito;Taiki Abe;K. Tanino
摘要以三异丙基硅基三氟甲磺酸盐和2,2,6,6-四甲基哌啶为原料，在温和的非碱性中性条件下与醛直接加成，得到收率较高的β-羟基腈三异丙基硅基醚。该反应是通过从烷腈原位生成n -硅基烯基亚胺中间体，然后将中间体亲核加成到醛上进行的。
Abstract Upon treatment with triisopropylsilyl trifluoromethanesulfonate and 2,2,6,6-tetramethylpiperidine, alkanenitriles undergo direct addition to aldehydes under mild non-basic neutral conditions to provide triisopropylsilyl ethers of β-hydroxy nitriles in good yield. The reaction proceeds through generation of an N-silyl ketene imine intermediate in situ from the alkanenitrile followed by nucleophilic addition of the intermediate to the aldehyde.