Department of Medicinal Chemistry, College of Pharmacy, The Third Military Medical University, Chongqing 400038, China.
Chem Soc Rev. 2012 Jun 7;41(11):4101-12. doi: 10.1039/c2cs35017c. Epub 2012 Mar 28.
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.
手性路易斯碱叔胺或膦可以使适当修饰的 Morita-Baylis-Hillman (MBH) 加合物与各种亲核试剂进行不对称烯丙基取代反应。此外，在布朗斯台德碱的辅助下，手性路易斯碱还可以催化将修饰的 MBH 加合物转化为烯丙基叶立德，这些叶立德可以参与各种不对称环化反应。本综述将重点介绍过去五年中 MBH 加合物的这种手性路易斯碱催化的不对称转化，这些转化可以快速构建具有高区域和立体选择性的高度官能化的手性分子。
