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Cationic Carbohydroxylation of Alkenes and Alkynes Using the Cation Pool Method

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posted on 05.08.2004, 00:00 by Seiji Suga, Yasuhisa Kageyama, Govindarajulu Babu, Kenichiro Itami, Jun-ichi Yoshida
The reactions of an N-acyliminium ion pool with alkenes and alkynes gave γ-amino alcohols and β-amino carbonyl compounds, respectively, after treatment with H2O/Et3N. The present reaction serves as an efficient method for cationic carbohydroxylation of alkenes and alkynes. When vinyltrimethylsilane was used as an alkene, the reaction was highly diastereoselective and served as an access to an enantiomerically pure α-silyl-γ-amino alcohol.