Aminocatalytic asymmetric Diels-Alder reaction of phosphorus dienophiles and 2,4-dienals

Chiral compounds bearing a phosphorus functional group are valuable because of their wide application in biological studies and asymmetric catalysis. Here we present an asymmetric Diels-Alder cycloaddition between phosphor-containing dienophiles and 2,4-dienals under the catalysis of chiral amine I via the intermediacy of trienamine species (trienamine catalysis). A spectrum of densely functionalized phosphonocyclohexene derivatives was efficiently constructed in excellent enantioselectivity (up to 99% ee) and with good to high diastereoselectivity (up to >19:1). (C) 2013 Elsevier Ltd. All rights reserved.