“…The addition of a carbocation to a carbon−carbon multiple bond, followed by the quenching of the resulting carbocation by water, also serves as a good and efficient method for carbohydroxylation (Scheme ). However, only a few papers on cationic carbohydroxylation have appeared in the literature , Stimulated by the straightforwardness of this approach, we have investigated cationic carbohydroxylation using the “cation pool” method 8 that we have recently developed and report here our findings. 1 Cationic Carbohydroxylation…”
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]
“…The addition of a carbocation to a carbon−carbon multiple bond, followed by the quenching of the resulting carbocation by water, also serves as a good and efficient method for carbohydroxylation (Scheme ). However, only a few papers on cationic carbohydroxylation have appeared in the literature , Stimulated by the straightforwardness of this approach, we have investigated cationic carbohydroxylation using the “cation pool” method 8 that we have recently developed and report here our findings. 1 Cationic Carbohydroxylation…”
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]
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