Regio- and stereoselective additions of diphenyldithiophosphinic acid to N-(1-alkynyl)amides and 1-alkynyl sulfides

Shigenari Kanemura; Azusa Kondoh; Hiroto Yasui; Hideki Yorimitsu; Koichiro Oshima

doi:10.1246/bcsj.81.506

Regio- and stereoselective additions of diphenyldithiophosphinic acid to N-(1-alkynyl)amides and 1-alkynyl sulfides

Shigenari Kanemura, Azusa Kondoh, Hiroto Yasui, Hideki Yorimitsu, Koichiro Oshima

SCI - Research and Analytical Center for Giant Molecules

Kyoto University

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

23 Citations (Scopus)

Abstract

Treatment of N-(l-alkynyl)amides and 1-alkynyl sulfides with diphenyldithiophosphinic acid affords (E)-ketene N,S-acetals and S.S-acetals, respectively. The addition reactions proceed in syn fashions, which consist of protonation of the electron-rich alkynes and the following nucleophilic addition of diphenyldithiophosphinate anion to the resulting cationic intermediates.

Original language	English
Pages (from-to)	506-514
Number of pages	9
Journal	Bulletin of the Chemical Society of Japan
Volume	81
Issue number	4
DOIs	https://doi.org/10.1246/bcsj.81.506
Publication status	Published - 2008

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abstract = "Treatment of N-(l-alkynyl)amides and 1-alkynyl sulfides with diphenyldithiophosphinic acid affords (E)-ketene N,S-acetals and S.S-acetals, respectively. The addition reactions proceed in syn fashions, which consist of protonation of the electron-rich alkynes and the following nucleophilic addition of diphenyldithiophosphinate anion to the resulting cationic intermediates.",

author = "Shigenari Kanemura and Azusa Kondoh and Hiroto Yasui and Hideki Yorimitsu and Koichiro Oshima",

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T1 - Regio- and stereoselective additions of diphenyldithiophosphinic acid to N-(1-alkynyl)amides and 1-alkynyl sulfides

AU - Kanemura, Shigenari

AU - Kondoh, Azusa

AU - Yasui, Hiroto

AU - Yorimitsu, Hideki

AU - Oshima, Koichiro

PY - 2008

Y1 - 2008

N2 - Treatment of N-(l-alkynyl)amides and 1-alkynyl sulfides with diphenyldithiophosphinic acid affords (E)-ketene N,S-acetals and S.S-acetals, respectively. The addition reactions proceed in syn fashions, which consist of protonation of the electron-rich alkynes and the following nucleophilic addition of diphenyldithiophosphinate anion to the resulting cationic intermediates.

AB - Treatment of N-(l-alkynyl)amides and 1-alkynyl sulfides with diphenyldithiophosphinic acid affords (E)-ketene N,S-acetals and S.S-acetals, respectively. The addition reactions proceed in syn fashions, which consist of protonation of the electron-rich alkynes and the following nucleophilic addition of diphenyldithiophosphinate anion to the resulting cationic intermediates.

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JO - Bulletin of the Chemical Society of Japan

JF - Bulletin of the Chemical Society of Japan

IS - 4

ER -

Regio- and stereoselective additions of diphenyldithiophosphinic acid to N-(1-alkynyl)amides and 1-alkynyl sulfides

Abstract

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