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

被引：32
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
收藏
页码：3995 / 3999
页数：5
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