Organocatalytic asymmetric transformations of modified Morita-Baylis-Hillman adducts

Chiral Lewis basic tertiary amines or phosphines can enable properly modified Morita-Baylis-Hillman (MBH) adducts to undergo asymmetric allylic substitutions with a wide range of nucleophiles. In addition, assisted by a Brønsted base, chiral Lewis bases can also catalytically convert modified MBH ad...

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Veröffentlicht in:Chemical Society reviews 2012-01, Vol.41 (11), p.411-4112
Hauptverfasser: Liu, Tian-Yu, Xie, Min, Chen, Ying-Chun
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description Chiral Lewis basic tertiary amines or phosphines can enable properly modified Morita-Baylis-Hillman (MBH) adducts to undergo asymmetric allylic substitutions with a wide range of nucleophiles. In addition, assisted by a Brønsted base, chiral Lewis bases can also catalytically convert modified MBH adducts into allylic ylides, which can be engaged in a variety of asymmetric annulation reactions. This tutorial review will focus on such chiral Lewis base-catalysed asymmetric transformations of MBH adducts, especially those developed over the past five years, allowing for the rapid construction of densely functionalised chiral molecules with high levels of regio- and stereoselectivities. This tutorial review summarises the asymmetric allylic alkylations or [3 + 2] annulations with racemic modified Morita-Baylis-Hillman adducts by the catalysis of chiral Lewis basic amines or phosphines.
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source MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects Alkylation
Amines - chemistry
Catalysis
Cyclization
Lewis Bases - chemistry
Phosphines - chemistry
Stereoisomerism
title Organocatalytic asymmetric transformations of modified Morita-Baylis-Hillman adducts
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