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 journalArticle

46 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 languageEnglish
Pages (from-to)2709-2711
Number of pages3
JournalOrganic Letters
Volume6
Issue number16
DOIs
Publication statusPublished - Aug 5 2004
Externally publishedYes

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Alkynes
Alkenes
alkynes
Amino Alcohols
alkenes
Cations
cations
alcohols
Carbonyl compounds
carbonyl compounds
Ions
ions

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Cationic carbohydroxylation of alkenes and alkynes using the cation pool method. / Suga, Seiji; Kageyama, Yasuhisa; Babu, Govindarajulu; Itami, Kenichiro; Yoshida, Jun Ichi.

In: Organic Letters, Vol. 6, No. 16, 05.08.2004, p. 2709-2711.

Research output: Contribution to journalArticle

Suga, S, Kageyama, Y, Babu, G, Itami, K & Yoshida, JI 2004, 'Cationic carbohydroxylation of alkenes and alkynes using the cation pool method', Organic Letters, vol. 6, no. 16, pp. 2709-2711. https://doi.org/10.1021/ol049049q
Suga, Seiji ; Kageyama, Yasuhisa ; Babu, Govindarajulu ; Itami, Kenichiro ; Yoshida, Jun Ichi. / Cationic carbohydroxylation of alkenes and alkynes using the cation pool method. In: Organic Letters. 2004 ; Vol. 6, No. 16. pp. 2709-2711.
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