Department of Organic Chemistry, Universidad Autónoma de Madrid, Cantoblanco, 28049.
Org Biomol Chem. 2011 Dec 21;9(24):8253-60. doi: 10.1039/c1ob06356a. Epub 2011 Nov 1.
The presence of a p-nitrophenyl group converts acetone into an excellent and versatile nucleophile in organocatalytic processes, able to react with α,β-unsaturated aldehydes affording β-substituted α-arylcyclohexenones via a Michael reaction/aldol reaction/dehydration sequence, which occurs in good yields, ee up to 96% and complete diastereoselectivity. The resulting compounds are excellent synthons for the diastereoselective preparation of a variety of synthetically useful polysubstituted cyclohexanones and derivatives.
当存在对硝基苯基时，丙酮在有机催化过程中会转变成一种出色且用途广泛的亲核试剂，能够与α,β-不饱和醛反应，通过迈克尔加成/羟醛缩合/脱水序列生成β-取代的α-芳基环己烯酮，产率良好，ee 值高达 96%，且具有完全的非对映选择性。所得化合物是用于非对映选择性制备各种合成有用的多取代环己酮和衍生物的优秀前体。
