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

Mondal, Santigopal ; Mukherjee, Subrata ; Das, Tamal Kanti ; Gonnade, Rajesh ; Biju, Akkattu T. (2017) N-Heterocyclic Carbene-Catalyzed Aldol-Lactonization of Ketoacids via Dynamic Kinetic Resolution ACS Catalysis, 7 (6). pp. 3995-3999. ISSN 2155-5435

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Official URL: http://doi.org/10.1021/acscatal.7b00681

Related URL: http://dx.doi.org/10.1021/acscatal.7b00681

Abstract

N-Heterocyclic carbene (NHC)-catalyzed enantioselective aldol lactonization of acyclic ketoacids, proceeding via dynamic kinetic resolution, is presented. The carbene generated from the chiral aminoindanol-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 β-lactones having three contiguous stereocenters. The reaction products are shown to undergo substrate-controlled β-lactone opening in the presence of amines to afford succinimide derivatives with four contiguous stereocenters.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society
ID Code:128648
Deposited On:03 Nov 2022 06:50
Last Modified:03 Nov 2022 06:50

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