A Bronsted acid mediated cascade enone synthesis from aldehydes containing a tethered propargylsilane

Rui Ramalho; Peter Jervis; Benson Kariuki; AG Humphries; Liam Cox

doi:10.1021/jo702351s

A Bronsted acid mediated cascade enone synthesis from aldehydes containing a tethered propargylsilane

Rui Ramalho, Peter Jervis, Benson Kariuki, AG Humphries, Liam Cox

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Abstract

[GRAPHICS] MeSO3H effects the intramolecular allenylation of a series of aldehydes I to provide allenyl alcohol product 3 as a single diastereoisomer. Cyclization proceeds rapidly at -78 degrees C. However, when the reaction is performed at room temperature, aldehyde 1 provides enone product 7 instead. A mechanism for the formation of this product is proposed in which the initially formed allenyl alcohol, 3 undergoes dehydration to provide an allyl carbocation, which is trapped with water, thereby installing the enone.

Original language	English
Pages (from-to)	1631-1634
Number of pages	4
Journal	The Journal of Organic Chemistry
Volume	73
Issue number	4
DOIs	https://doi.org/10.1021/jo702351s
Publication status	Published - 1 Jan 2008

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abstract = "[GRAPHICS] MeSO3H effects the intramolecular allenylation of a series of aldehydes I to provide allenyl alcohol product 3 as a single diastereoisomer. Cyclization proceeds rapidly at -78 degrees C. However, when the reaction is performed at room temperature, aldehyde 1 provides enone product 7 instead. A mechanism for the formation of this product is proposed in which the initially formed allenyl alcohol, 3 undergoes dehydration to provide an allyl carbocation, which is trapped with water, thereby installing the enone.",

author = "Rui Ramalho and Peter Jervis and Benson Kariuki and AG Humphries and Liam Cox",

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T1 - A Bronsted acid mediated cascade enone synthesis from aldehydes containing a tethered propargylsilane

AU - Ramalho, Rui

AU - Jervis, Peter

AU - Kariuki, Benson

AU - Humphries, AG

AU - Cox, Liam

PY - 2008/1/1

Y1 - 2008/1/1

N2 - [GRAPHICS] MeSO3H effects the intramolecular allenylation of a series of aldehydes I to provide allenyl alcohol product 3 as a single diastereoisomer. Cyclization proceeds rapidly at -78 degrees C. However, when the reaction is performed at room temperature, aldehyde 1 provides enone product 7 instead. A mechanism for the formation of this product is proposed in which the initially formed allenyl alcohol, 3 undergoes dehydration to provide an allyl carbocation, which is trapped with water, thereby installing the enone.

AB - [GRAPHICS] MeSO3H effects the intramolecular allenylation of a series of aldehydes I to provide allenyl alcohol product 3 as a single diastereoisomer. Cyclization proceeds rapidly at -78 degrees C. However, when the reaction is performed at room temperature, aldehyde 1 provides enone product 7 instead. A mechanism for the formation of this product is proposed in which the initially formed allenyl alcohol, 3 undergoes dehydration to provide an allyl carbocation, which is trapped with water, thereby installing the enone.

U2 - 10.1021/jo702351s

DO - 10.1021/jo702351s

M3 - Article

C2 - 18197686

VL - 73

SP - 1631

EP - 1634

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

IS - 4

ER -

A Bronsted acid mediated cascade enone synthesis from aldehydes containing a tethered propargylsilane

Abstract

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