N-Heterocyclic Carbene-Catalyzed Aldol-Lactonization of Ketoacids via Dynamic Kinetic Resolution

被引：30

作者：

Mondal, Santigopal ^{[1
,3
]}

Mukherjee, Subrata ^{[1
,3
]}

Das, Tamal Kanti ^{[1
,3
]}

Gonnade, Rajesh ^{[2
]}

Biju, Akkattu T. ^{[1
,3
]}

机构：

[1] NCL, CSIR, Organ Chem Div, Dr Homi Bhabha Rd, Pune 411008, Maharashtra, India

[2] NCL, CSIR, Ctr Mat Characterizat, Dr Homi Bhabha Rd, Pune 411008, Maharashtra, India

[3] AcSIR, New Delhi 110020, India

来源：

ACS CATALYSIS | 2017年 / 7卷 / 06期

关键词：

N-heterocyclic carbenes; organocatalysis; aldol lactonization; beta-lactones; DKR strategies; ketoacids; BICYCLIC-BETA-LACTONES; BOND-FORMING REACTIONS; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; LEWIS-ACID; ACYL AZOLIUMS; FUNCTIONALIZED CYCLOPENTENES; GAMMA-BUTYROLACTONES; CARBOXYLIC-ACIDS; RACEMIC MIXTURES;

D O I：

10.1021/acscatal.7b00681

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

N-Heteroryclic carbene (NHC)-catalyzed enantioselective aldol lactonization of acyclic ketoacids, proceeding via dynamic kinetic resolution, is presented. The carbene generated from the chiral anninoinclanol-derived triazolium salt in the presence of LiCl was the key for the success of this transformation. The reaction allowed the diastereoselective and enantioselective synthesis of cyclopentane-fused beta-lactones having three contiguous stereocenters. The reaction products are shown to undergo substrate-controlled beta-lactone opening in the presence of amines to afford succinimide derivatives with four contiguous stereocenters.

引用

页码：3995 / 3999

页数：5

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