Cationic carbohydroxylation of alkenes and alkynes using the cation pool method

Seiji Suga; Yasuhisa Kageyama; Govindarajulu Babu; Kenichiro Itami; Jun Ichi Yoshida

doi:10.1021/ol049049q

Cationic carbohydroxylation of alkenes and alkynes using the cation pool method

Seiji Suga, Yasuhisa Kageyama, Govindarajulu Babu, Kenichiro Itami, Jun Ichi Yoshida

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	2709-2711
Number of pages	3
Journal	Organic Letters
Volume	6
Issue number	16
DOIs	https://doi.org/10.1021/ol049049q
Publication status	Published - Aug 5 2004
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol049049q

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abstract = "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.",

author = "Seiji Suga and Yasuhisa Kageyama and Govindarajulu Babu and Kenichiro Itami and Yoshida, {Jun Ichi}",

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T1 - Cationic carbohydroxylation of alkenes and alkynes using the cation pool method

AU - Suga, Seiji

AU - Kageyama, Yasuhisa

AU - Babu, Govindarajulu

AU - Itami, Kenichiro

AU - Yoshida, Jun Ichi

PY - 2004/8/5

Y1 - 2004/8/5

N2 - 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.

AB - 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.

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JO - Organic Letters

JF - Organic Letters

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ER -

Cationic carbohydroxylation of alkenes and alkynes using the cation pool method

Abstract

ASJC Scopus subject areas

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