Cationic carbohydroxylation of alkenes and alkynes using the cation pool method.
The reactions of an N-acyliminium ion pool with alkenes and alkynes gave gamma-amino alcohols and beta-amino carbonyl compounds, respectively, after treatment with H(2)O/Et(3)N. 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 alpha-silyl-gamma-amino alcohol. [reaction: see text]
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.
Seiji
S
Suga
Yasuhisa
Y
Kageyama
Govindarajulu
G
Babu
Kenichiro
K
Itami
Jun-ichi
J
Yoshida