Asymmetric organocatalytic 1,6-conjugate addition of aldehydes to dienic sulfones

John J. Murphy; Adrien Quintard; Patrick McArdle; Alexandre Alexakis; John C. Stephens

doi:10.1002/anie.201100804

Asymmetric organocatalytic 1,6-conjugate addition of aldehydes to dienic sulfones

John J. Murphy, Adrien Quintard, Patrick McArdle, Alexandre Alexakis, John C. Stephens

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

70 Citations (Scopus)

Abstract

An unprecedented 1,6-enamine conjugate addition exploiting the charge delocalization in 1,3-bis(sulfonyl) butadienes has been developed. By appropriately designing a Michael acceptor, unique reactivities were obtained for the formation of highly valuable dienes containing two versatile vinyl sulfones (see scheme, TMS=trimethylsilyl).

Original language	English
Pages (from-to)	5095-5098
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	50
Issue number	22
DOIs	https://doi.org/10.1002/anie.201100804
Publication status	Published - 23 May 2011
Externally published	Yes

Keywords

asymmetric synthesis
conjugate addition
dienes
organocatalysis
sulfones

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10.1002/anie.201100804

Cite this

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abstract = "An unprecedented 1,6-enamine conjugate addition exploiting the charge delocalization in 1,3-bis(sulfonyl) butadienes has been developed. By appropriately designing a Michael acceptor, unique reactivities were obtained for the formation of highly valuable dienes containing two versatile vinyl sulfones (see scheme, TMS=trimethylsilyl).",

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AU - Murphy, John J.

AU - Quintard, Adrien

AU - McArdle, Patrick

AU - Alexakis, Alexandre

AU - Stephens, John C.

PY - 2011/5/23

Y1 - 2011/5/23

N2 - An unprecedented 1,6-enamine conjugate addition exploiting the charge delocalization in 1,3-bis(sulfonyl) butadienes has been developed. By appropriately designing a Michael acceptor, unique reactivities were obtained for the formation of highly valuable dienes containing two versatile vinyl sulfones (see scheme, TMS=trimethylsilyl).

AB - An unprecedented 1,6-enamine conjugate addition exploiting the charge delocalization in 1,3-bis(sulfonyl) butadienes has been developed. By appropriately designing a Michael acceptor, unique reactivities were obtained for the formation of highly valuable dienes containing two versatile vinyl sulfones (see scheme, TMS=trimethylsilyl).

KW - asymmetric synthesis

KW - conjugate addition

KW - dienes

KW - organocatalysis

KW - sulfones

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U2 - 10.1002/anie.201100804

DO - 10.1002/anie.201100804

M3 - Article

SN - 1433-7851

VL - 50

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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ER -

Asymmetric organocatalytic 1,6-conjugate addition of aldehydes to dienic sulfones

Abstract

Keywords

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