The Journal of Organic Chemistry

Highly Regio-and Diastereoselective One-Pot Synthesis of Silyl Epoxy Alcohols and Vinylsilanes by Direct Hydroxy-Epoxidation

W Adam, MJ Richter

文献索引：Adam, Waldemar; Richter, Markus J. Journal of Organic Chemistry, 1994 , vol. 59, # 12 p. 3341 - 3346

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被引用次数: 14

摘要

A direct synthesis of silyl epoxy alcohols from vinylsilanes is described. It consists of the regioselective ene reaction of the vinylsilanes with singlet oxygen, which proceeds with predominant hydrogen abstraction at the position geminal to the silyl group. The resulting silyl allylic hydroperoxides were treated, without isolation, subsequently with Ti (0-i-Pr) d to afford the silyl epoxy alcohols in good yields and very high diastereomeric ratios, which ...