Kaur Ravneet, Rautela Saurabh Singh, Ali Mubarik, Singh Ravi P
Department of Chemistry, Indian Institute of Technology Delhi, Hauz Khas, New Delhi 110016, India.
J Org Chem. 2024 Oct 4;89(19):14177-14182. doi: 10.1021/acs.joc.4c01570. Epub 2024 Sep 18.
An approach involving the use of a bifunctional aminocatalyst containing Brønsted base and iminium activation sites for asymmetric multicomponent reactions involving [1,2]-phospha-Brook rearrangement has yet to be realized. Herein, we present an aminocatalytic enantioselective conjugate addition of α-phosphonyloxy enolates formed [1,2]-phospha-Brook rearrangement to α,β-unsaturated ketones. The methodology unfolds a simple one-pot operation consisting of a robust additive-free catalytic system providing a series of oxindole derivatives having two contiguous stereocenters in high yields with excellent stereoselectivities.
一种涉及使用含有布朗斯特碱和亚胺离子活化位点的双功能氨基催化剂用于涉及[1,2]-磷杂-Brook重排的不对称多组分反应的方法尚未实现。在此，我们报道了一种氨基催化的对映选择性共轭加成反应，即由[1,2]-磷杂-Brook重排形成的α-膦酰氧基烯醇盐与α,β-不饱和酮的反应。该方法展现出一种简单的一锅操作，由一个强大的无添加剂催化体系组成，能以高产率和优异的立体选择性提供一系列具有两个相邻立体中心的氧化吲哚衍生物。
