铜催化的亚胺叶立德与β-苯磺酰基烯酮的不对称 1,3-偶极环加成。手性配体控制的非对映选择性反转。

Cu-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with beta-phenylsulfonyl enones. Ligand controlled diastereoselectivity reversal.

机构信息

Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain.

出版信息

J Org Chem. 2010 Jan 1;75(1):233-6. doi: 10.1021/jo902103z.

DOI:10.1021/jo902103z

Abstract

A catalytic asymmetric procedure for the 1,3-dipolar cycloaddition of (E)-beta-phenylsulfonyl enones with azomethine ylides to provide highly functionalized pyrrolidine derivatives is described. In the presence of chiral Cu(I)-Segphos catalysts the adducts were obtained with high regio-, diastereo-, and enantioselectivity. Interestingly, a switch from endo to exo selectivity was observed when Segphos or DTBM-Segphos ligand was used.

摘要

描述了一种催化不对称的 1,3-偶极环加成反应，用于（E）-β-苯磺酰烯酮与亚胺叶立德的反应，以提供高官能化的吡咯烷衍生物。在手性 Cu(I)-Segphos 催化剂的存在下，加成物具有高区域选择性、非对映选择性和对映选择性。有趣的是，当使用 Segphos 或 DTBM-Segphos 配体时，选择性从内型到外型发生了转变。

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