Literature DB >> 14709036

Catalytic asymmetric acyl halide-aldehyde cyclocondensation reactions of substituted ketenes.

Scott G Nelson1, Cheng Zhu, Xiaoqiang Shen.   

Abstract

Catalytic asymmetric acyl halide-aldehyde cyclocondensation (AAC) reactions of alkyl-substituted ketenes with structurally diverse aldehydes provide cis-disubstituted beta-lactones with high enantioselectivity. The AAC reactions utilize a novel Al(III)-triamine catalyst in which the metal's dynamic coordination geometry leads to a highly selective catalyst complex. These AAC reactions represent a functional solution to highly enantioselective substituted ester enolate aldol additions.

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Year:  2004        PMID: 14709036     DOI: 10.1021/ja0391208

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


  6 in total

1.  Rapid assembly of complex cyclopentanes employing chiral, α,β-unsaturated acylammonium intermediates.

Authors:  Gang Liu; Morgan E Shirley; Khoi N Van; Rae Lynn McFarlin; Daniel Romo
Journal:  Nat Chem       Date:  2013-11-03       Impact factor: 24.427

2.  Remote stereoinduction in the acylation of fully substituted enolates: tandem Reformatsky/quaternary Claisen condensations of silyl glyoxylates and β-lactones.

Authors:  Stephen N Greszler; Justin T Malinowski; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2010-11-18       Impact factor: 15.419

3.  Formal synthesis of leustroducsin B via Reformatsky/Claisen condensation of silyl glyoxylates.

Authors:  Stephen N Greszler; Justin T Malinowski; Jeffrey S Johnson
Journal:  Org Lett       Date:  2011-05-17       Impact factor: 6.005

4.  1,4-Aryl migration in ketene-derived enolates by a polar-radical-crossover cascade.

Authors:  Niklas Radhoff; Armido Studer
Journal:  Nat Commun       Date:  2022-06-02       Impact factor: 17.694

5.  Cooperative Al(salen)-pyridinium catalysts for the asymmetric synthesis of trans-configured β-lactones by [2+2]-cyclocondensation of acylbromides and aldehydes: investigation of pyridinium substituent effects.

Authors:  Patrick Meier; Florian Broghammer; Katja Latendorf; Guntram Rauhut; René Peters
Journal:  Molecules       Date:  2012-06-12       Impact factor: 4.411

Review 6.  Progress in the total synthesis of inthomycins.

Authors:  Bidyut Kumar Senapati
Journal:  Beilstein J Org Chem       Date:  2021-01-07       Impact factor: 2.883

  6 in total

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