Phosphine-catalyzed allylic substitution of Morita-Baylis-Hillman acetates: Synthesis of n-protected β-aminophosphonic acid esters

Haell Park; Chang Woo Cho; Michael J. Krische

doi:10.1021/jo061218s

Phosphine-catalyzed allylic substitution of Morita-Baylis-Hillman acetates: Synthesis of n-protected β-aminophosphonic acid esters

Haell Park, Chang Woo Cho, Michael J. Krische

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Abstract

(Chemical Equation Presented) A series of N-protected β-amino phosphonic acid esters have been prepared by phosphine-catalyzed allylic substitution of 2-(diethylphosphonyl)-substituted allylic acetates employing 4,5-dichlorophthalimide as nucleophilic partner. These organocatalytic allylic substitutions exhibit exceptionally high levels of regiospecificity by virtue of a tandem S_N2′-S_N2′ mechanism.

Original language	English
Pages (from-to)	7892-7894
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	71
Issue number	20
DOIs	https://doi.org/10.1021/jo061218s
State	Published - 29 Sep 2006

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title = "Phosphine-catalyzed allylic substitution of Morita-Baylis-Hillman acetates: Synthesis of n-protected β-aminophosphonic acid esters",

abstract = "(Chemical Equation Presented) A series of N-protected β-amino phosphonic acid esters have been prepared by phosphine-catalyzed allylic substitution of 2-(diethylphosphonyl)-substituted allylic acetates employing 4,5-dichlorophthalimide as nucleophilic partner. These organocatalytic allylic substitutions exhibit exceptionally high levels of regiospecificity by virtue of a tandem SN2′-SN2′ mechanism.",

author = "Haell Park and Cho, {Chang Woo} and Krische, {Michael J.}",

year = "2006",

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T2 - Synthesis of n-protected β-aminophosphonic acid esters

AU - Park, Haell

AU - Cho, Chang Woo

AU - Krische, Michael J.

PY - 2006/9/29

Y1 - 2006/9/29

N2 - (Chemical Equation Presented) A series of N-protected β-amino phosphonic acid esters have been prepared by phosphine-catalyzed allylic substitution of 2-(diethylphosphonyl)-substituted allylic acetates employing 4,5-dichlorophthalimide as nucleophilic partner. These organocatalytic allylic substitutions exhibit exceptionally high levels of regiospecificity by virtue of a tandem SN2′-SN2′ mechanism.

AB - (Chemical Equation Presented) A series of N-protected β-amino phosphonic acid esters have been prepared by phosphine-catalyzed allylic substitution of 2-(diethylphosphonyl)-substituted allylic acetates employing 4,5-dichlorophthalimide as nucleophilic partner. These organocatalytic allylic substitutions exhibit exceptionally high levels of regiospecificity by virtue of a tandem SN2′-SN2′ mechanism.

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Phosphine-catalyzed allylic substitution of Morita-Baylis-Hillman acetates: Synthesis of n-protected β-aminophosphonic acid esters

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