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Literature DB >> 17252120

Recent approaches towards the asymmetric synthesis of alpha,alpha-disubstituted alpha-amino acids.

Abstract

The class of alpha,alpha-disubstituted alpha-amino acids has gained considerable attention in the past decades and continues doing so. The ongoing interest in biological and chemical properties of the substance class has inspired the development of many new methodologies for their asymmetric construction, which have not found their way into the general focus of organic chemistry yet. The aim of this review is to provide an overview of the developments in the field since 1998.

Entities: Chemical

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Year: 2006 PMID： 17252120 DOI： 10.1039/b611091f

Source DB: PubMed Journal: Org Biomol Chem ISSN： 1477-0520 Impact factor: 3.876

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Cited

22 in total

1. Enantioselective nucleophilic catalysis: the synthesis of aza-beta-lactams through [2+2] cycloadditions of ketenes with azo compounds.

Authors: Jacob M Berlin; Gregory C Fu
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

2. Enantioselective alpha-amination of 1,3-dicarbonyl compounds using squaramide derivatives as hydrogen bonding catalysts.

Authors: Hideyuki Konishi; Tin Yiu Lam; Jeremiah P Malerich; Viresh H Rawal
Journal: Org Lett Date: 2010-05-07 Impact factor: 6.005

10. Synthesis of enantiomerically enriched (R)-C-labelled 2-aminoisobutyric acid (Aib) by conformational memory in the alkylation of a derivative of L-alanine.

Authors: Stephen P Fletcher; Jordi Solà; Dean Holt; Robert A Brown; Jonathan Clayden
Journal: Beilstein J Org Chem Date: 2011-09-20 Impact factor: 2.883

Recent approaches towards the asymmetric synthesis of alpha,alpha-disubstituted alpha-amino acids.

1. Enantioselective nucleophilic catalysis: the synthesis of aza-beta-lactams through [2+2] cycloadditions of ketenes with azo compounds.

2. Enantioselective alpha-amination of 1,3-dicarbonyl compounds using squaramide derivatives as hydrogen bonding catalysts.

3. A Broad Substrate Scope of Aza-Friedel-Crafts Alkylation for the Synthesis of Quaternary α-Amino Esters.

4. Recent Progress on the Stereoselective Synthesis of Cyclic Quaternary alpha-Amino Acids.

5. Catalytic, Enantioselective α-Alkylation of Azlactones with Nonconjugated Alkenes by Directed Nucleopalladation.

6. Conformational preferences of alpha-substituted proline analogues.

7. Synthesis of Boc-protected bicycloproline.

8. Stereoselective Synthesis of Quaternary Proline Analogues.

9. Enantioselective Addition of α-Nitroesters to Alkynes.

10. Synthesis of enantiomerically enriched (R)-C-labelled 2-aminoisobutyric acid (Aib) by conformational memory in the alkylation of a derivative of L-alanine.