Synthesis of α-alkylated γ-butyrolactones with concomitant anhydride kinetic resolution using a sulfamide-based catalyst

被引：7

作者：

Claveau, Romain ^{[1
]}

Twamley, Brendan ^{[1
]}

Connon, Stephen J. ^{[1
]}

机构：

[1] Trinity Coll Dublin, Trinity Biomed Sci Inst, Sch Chem, 152-160 Pearse St, Dublin 2, Ireland

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2018年 / 16卷 / 41期

基金：

爱尔兰科学基金会;

关键词：

ASYMMETRIC TAMURA CYCLOADDITIONS; CYCLIC ANHYDRIDES; BIFUNCTIONAL ORGANOCATALYSTS; MICHAEL ADDITION; METHANOLYTIC DESYMMETRIZATION; QUATERNARY STEREOCENTERS; HOMOPHTHALIC ANHYDRIDE; FORMAL CYCLOADDITIONS; NATURAL-PRODUCTS; DERIVATIVES;

D O I：

10.1039/c8ob02248h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Kinetic Resolution (KR) of -alkylated enolisable disubstituted anhydrides has been shown to be possible for the first time. In the presence of an ad hoc designed novel class of bifunctional sulfamide organocatalyst, a regio-, diastereo- and enantioselective cycloaddition reaction between the enolisable anhydride and benzaldehydes provides densely functionalised -butyrolactones in one pot (up to 19:1 dr, 94% ee) with control over three contiguous stereocentres. The concomitant resolution of the starting material anhydride, provides access to a range of chiral succinate derivatives with selectivity factors up to S* = 10.5.

引用

页码：7574 / 7578

页数：5

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