Cooperativity in the counterion catalysis of Morita/Baylis/Hillman reactions promoted by enantioselective trifunctional organocatalysts

Christopher Anstiss; Fei Liu

doi:10.1016/j.tet.2010.05.007

Cooperativity in the counterion catalysis of Morita/Baylis/Hillman reactions promoted by enantioselective trifunctional organocatalysts

Christopher Anstiss, Fei Liu^*

^*Corresponding author for this work

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

23 Citations (Scopus)

Abstract

New trifunctional organocatalysts with a NHTs Brønsted acid were prepared and tested in their ability to promote the counterion catalysis of generic and aza-Morita/Baylis/Hillman reactions.The cooperativity between the counterion and the NHTs Brønsted acid of the trifunctional catalyst was required for good enantioselectivity and rate enhancement.Better enantioselectivity was observed for aza-MBH reactions at relatively low catalyst loading (2-5 mol %) under facile conditions.

Original language	English
Pages (from-to)	5486-5491
Number of pages	6
Journal	Tetrahedron
Volume	66
Issue number	29
DOIs	https://doi.org/10.1016/j.tet.2010.05.007
Publication status	Published - 17 Jul 2010

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10.1016/j.tet.2010.05.007

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abstract = "New trifunctional organocatalysts with a NHTs Br{\o}nsted acid were prepared and tested in their ability to promote the counterion catalysis of generic and aza-Morita/Baylis/Hillman reactions.The cooperativity between the counterion and the NHTs Br{\o}nsted acid of the trifunctional catalyst was required for good enantioselectivity and rate enhancement.Better enantioselectivity was observed for aza-MBH reactions at relatively low catalyst loading (2-5 mol \%) under facile conditions.",

author = "Christopher Anstiss and Fei Liu",

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AU - Anstiss, Christopher

AU - Liu, Fei

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Y1 - 2010/7/17

N2 - New trifunctional organocatalysts with a NHTs Brønsted acid were prepared and tested in their ability to promote the counterion catalysis of generic and aza-Morita/Baylis/Hillman reactions.The cooperativity between the counterion and the NHTs Brønsted acid of the trifunctional catalyst was required for good enantioselectivity and rate enhancement.Better enantioselectivity was observed for aza-MBH reactions at relatively low catalyst loading (2-5 mol %) under facile conditions.

AB - New trifunctional organocatalysts with a NHTs Brønsted acid were prepared and tested in their ability to promote the counterion catalysis of generic and aza-Morita/Baylis/Hillman reactions.The cooperativity between the counterion and the NHTs Brønsted acid of the trifunctional catalyst was required for good enantioselectivity and rate enhancement.Better enantioselectivity was observed for aza-MBH reactions at relatively low catalyst loading (2-5 mol %) under facile conditions.

UR - https://www.scopus.com/pages/publications/77954315745

U2 - 10.1016/j.tet.2010.05.007

DO - 10.1016/j.tet.2010.05.007

M3 - Article

AN - SCOPUS:77954315745

SN - 0040-4020

VL - 66

SP - 5486

EP - 5491

JO - Tetrahedron

JF - Tetrahedron

IS - 29

ER -

Cooperativity in the counterion catalysis of Morita/Baylis/Hillman reactions promoted by enantioselective trifunctional organocatalysts

Abstract

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