Literature DB >> 12617633

An exceptionally mild catalytic thioester aldol reaction inspired by polyketide biosynthesis.

Gojko Lalic1, Allen D Aloise, Matthew D Shair.   

Abstract

This report details our discovery of a new catalytic ester aldol reaction using malonic acid half thioesters (MAHTs) that directly affords beta-hydroxythioesters. The reaction is catalyzed by combination of a Cu(II) salt and an amine base, and it can be performed under exceptionally mild conditions (23 degrees C, open to the air, wet solvent). Methyl malonic acid half thioesters afforded syn aldol products with distereoselectivities greater than 6:1.

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Year:  2003        PMID: 12617633     DOI: 10.1021/ja029452x

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  7 in total

1.  Copper(II)-Catalyzed Tandem Decarboxylative Michael/Aldol Reactions Leading to the Formation of Functionalized Cyclohexenones.

Authors:  Jeonghyo Lee; Sibin Wang; Miranda Callahan; Pavel Nagorny
Journal:  Org Lett       Date:  2018-03-21       Impact factor: 6.005

2.  Tandem Rh-catalysis: decarboxylative β-keto acid and alkyne cross-coupling.

Authors:  Faben A Cruz; Zhiwei Chen; Sarah I Kurtoic; Vy M Dong
Journal:  Chem Commun (Camb)       Date:  2016-04-04       Impact factor: 6.222

3.  Asymmetric organocatalytic decarboxylative Mannich reaction using β-keto acids: A new protocol for the synthesis of chiral β-amino ketones.

Authors:  Chunhui Jiang; Fangrui Zhong; Yixin Lu
Journal:  Beilstein J Org Chem       Date:  2012-08-13       Impact factor: 2.883

4.  One-pot odourless synthesis of thioesters via in situ generation of thiobenzoic acids using benzoic anhydrides and thiourea.

Authors:  Mohammad Abbasi; Reza Khalifeh
Journal:  Beilstein J Org Chem       Date:  2015-07-28       Impact factor: 2.883

5.  Selective nickel- and manganese-catalyzed decarboxylative cross coupling of some α,β-unsaturated carboxylic acids with cyclic ethers.

Authors:  Jia-Xiang Zhang; Yan-Jing Wang; Wei Zhang; Nai-Xing Wang; Cui-Bing Bai; Ya-Lan Xing; Yi-He Li; Jia-Long Wen
Journal:  Sci Rep       Date:  2014-12-12       Impact factor: 4.379

6.  A convenient enantioselective decarboxylative aldol reaction to access chiral α-hydroxy esters using β-keto acids.

Authors:  Zhiqiang Duan; Jianlin Han; Ping Qian; Zirui Zhang; Yi Wang; Yi Pan
Journal:  Beilstein J Org Chem       Date:  2014-04-29       Impact factor: 2.883

7.  Development of copper-catalyzed enantioselective decarboxylative aldolization for the preparation of perfluorinated 1,3,5-triols featuring supramolecular recognition properties.

Authors:  Céline Sperandio; Jean Rodriguez; Adrien Quintard
Journal:  Chem Sci       Date:  2019-12-27       Impact factor: 9.825

  7 in total

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