Double Nucleophilic Addition of Ketene Silyl Acetals to α,β-Unsaturated Imines: Factors Controlling the Regioselectivity

Makoto      Shimizu; Hiroshi      Kurokawa; Atsushi      Takahashi

doi:10.2174/1570178043400361

Abstract

The regioselectivity of the double nucleophilic addition of ketene silyl acetals to α,β-unsaturated imines was highly depended on the subtle difference of the reactivity of the ketene silyl acetals, and the factors were mainly derived from the ability of the ketene silyl acetals to undergo the silicon-aluminum exchange reaction, where the aluminum enolate preferentially underwent 1,4-addition.

Keywords: double nucleophilic addition, unsaturated imine, ketene silyl acetals

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Letters in Organic Chemistry

Title: Double Nucleophilic Addition of Ketene Silyl Acetals to α,β-Unsaturated Imines: Factors Controlling the Regioselectivity

Volume: 1 Issue: 4

Author(s): Makoto Shimizu, Hiroshi Kurokawa and Atsushi Takahashi

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Keywords: double nucleophilic addition, unsaturated imine, ketene silyl acetals

Abstract: The regioselectivity of the double nucleophilic addition of ketene silyl acetals to α,β-unsaturated imines was highly depended on the subtle difference of the reactivity of the ketene silyl acetals, and the factors were mainly derived from the ability of the ketene silyl acetals to undergo the silicon-aluminum exchange reaction, where the aluminum enolate preferentially underwent 1,4-addition.

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Shimizu Makoto, Kurokawa Hiroshi and Takahashi Atsushi, Double Nucleophilic Addition of Ketene Silyl Acetals to α,β-Unsaturated Imines: Factors Controlling the Regioselectivity, Letters in Organic Chemistry 2004; 1 (4) . https://dx.doi.org/10.2174/1570178043400361