非对映选择性和对映选择性曼尼希/环化级联反应在手性苯并噻唑嘧啶衍生物的构建中的应用。

Diastereo- and Enantioselective Mannich/Cyclization Cascade Reaction Access to Chiral Benzothiazolopyrimidine Derivatives.

机构信息

Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu, 610041, P. R. China.

Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai, 200433, P. R. China.

出版信息

Chemistry. 2021 Apr 7;27(20):6183-6186. doi: 10.1002/chem.202005509. Epub 2021 Mar 10.

DOI:10.1002/chem.202005509

PMID:33751688

Abstract

An efficient asymmetric Mannich/cyclization cascade strategy was established from 2-benzothiazolimines with N-acylpyrazoles to provide optical active benzothiazolopyrimidine derivatives using a copper-based complex. The mild cascade process constructed various structurally diverse products with broad scope of substrates together with excellent enantioselectivities (up to 99 % ee) and diastereoselectivities (up to 99:1 d.r.).

摘要

建立了一种高效的不对称 Mannich/环化级联策略，从 2-苯并噻唑亚胺和 N-酰基吡唑出发，使用铜基配合物提供光学活性苯并噻唑嘧啶衍生物。温和的级联过程构建了各种结构多样的产物，具有广泛的底物范围，同时具有优异的对映选择性（高达 99%ee）和非对映选择性（高达 99:1 d.r.）。