通过多催化仲胺/N-杂环卡宾催化的级联反应实现功能化环戊酮的不对称合成。
Asymmetric synthesis of functionalized cyclopentanones via a multicatalytic secondary amine/N-heterocyclic carbene catalyzed cascade sequence.
作者信息
Lathrop Stephen P, Rovis Tomislav
机构信息
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
出版信息
J Am Chem Soc. 2009 Sep 30;131(38):13628-30. doi: 10.1021/ja905342e.
Abstract
A one-pot, asymmetric multicatalytic formal [3+2] reaction between 1,3-dicarbonyls and alpha,beta-unsaturated aldehydes is described. The multicatalytic process involves a secondary amine catalyzed Michael addition followed by a N-heterocyclic carbene catalyzed intramolecular crossed benzoin reaction to afford densely functionalized cyclopentanones with high enantioselectivities. The reaction proceeds with a variety of alkyl and aryl enals as well as a range of 1,3-dicarbonyls (diketones and beta-ketoesters). The functionalized products are obtained from cheap, readily available starting materials in a rapid and efficient manner in a one-pot, one-step operation.
摘要
本文描述了一种在1,3 - 二羰基化合物与α,β - 不饱和醛之间进行的一锅法不对称多催化形式[3 + 2]反应。该多催化过程包括仲胺催化的迈克尔加成反应，随后是N - 杂环卡宾催化的分子内交叉安息香反应，以高对映选择性得到官能团密集的环戊酮。该反应适用于多种烷基和芳基烯醛以及一系列1,3 - 二羰基化合物（二酮和β - 酮酯）。官能化产物可通过一步一锅法操作，从廉价、易得的起始原料快速高效地获得。
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