Bulletin of the Chemical Society of Japan p. 528 - 532 (1983)
Update date:2022-08-04
Topics:
Matsuda, Isamu
Okada, Hisashi
Izumi, Yusuke
2-Substituted 2-alkenenitriles are obtained in the condensation reaction of carbonyl compounds with C,N-bis(trimethylsilyl)ketenimine in the presence of Lewis acid.The combination of tris(trimethylsilyl)ketenimine and aldehydes results in the high E-selective formation of 2-trimethylsilyl-2-alkenenitriles.Among some Lewis acids, magnesium bromid gives the best E-selectivity in the formation of 2-trimethylsilyl-2-undecenenitrile.Stereospecific protodesilylation of 2-trimethylsilyl-2-alkenenitriles in an aqueous methanol solution of potassium fluoride accomplishes a new route to (Z)-2-alkenenitriles from aldehydes.
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Doi:10.1021/ja046308y
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