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Organocatalytic asymmetric transformations of modified Morita-Baylis-Hillman adducts

Journal

CHEMICAL SOCIETY REVIEWS
Volume 41, Issue 11, Pages 4101-4112

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c2cs35017c

Keywords

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Funding

  1. National Natural Science Foundation of China [20972101, 21125206, 21021001]
  2. National Basic Research Program of China (973 Program) [2010CB833300]

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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 Bronsted 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.

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