Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 A new organocatalytic concept for asymmetric α-alkylation of aldehydes.

Literature DB >> 25369294

A new organocatalytic concept for asymmetric α-alkylation of aldehydes.

Lorenzo Caruana¹, Florian Kniep, Tore Kiilerich Johansen, Pernille H Poulsen, Karl Anker Jørgensen.

Abstract

The organocatalytic asymmetric α-alkylation of aldehydes by 1,6-conjugated addition of enamines to p-quinone methides is described. Employing a newly developed class of chiral secondary amine catalysts, α-diarylmethine-substituted aldehydes with two contiguous stereocenters have been synthesized in a simple manner with good diastereocontrol and excellent enantioselectivity.

Entities: Chemical

Year: 2014 PMID： 25369294 DOI： 10.1021/ja510475n

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

Keyword Cloud
Cited

13 in total

1. Cross-dehydrogenative coupling enables enantioselective access to CF₃-substituted all-carbon quaternary stereocenters.

Authors: Xiaoguang Pan; Zehua Wang; Linglong Kan; Ying Mao; Yasheng Zhu; Lei Liu
Journal: Chem Sci Date: 2020-01-29 Impact factor: 9.825

2. Copper-Catalyzed Borylative Aromatization of p-Quinone Methides: Enantioselective Synthesis of Dibenzylic Boronates.

Authors: Carlos Jarava-Barrera; Alejandro Parra; Aurora López; Fabio Cruz-Acosta; Daniel Collado-Sanz; Diego J Cárdenas; Mariola Tortosa
Journal: ACS Catal Date: 2015-12-11 Impact factor: 13.084

3. Organocatalytic one-pot 1,4-/1,6-/1,2-addition sequence for the stereocontrolled formation of six consecutive stereocenters.

Authors: Pankaj Chauhan; Suruchi Mahajan; Gerhard Raabe; Dieter Enders
Journal: Chem Commun (Camb) Date: 2015-02-11 Impact factor: 6.222

10. N-Heterocyclic carbenes as chiral Brønsted base catalysts: a highly diastereo- and enantioselective 1,6-addition reaction.

Authors: Surojit Santra; Arka Porey; Barun Jana; Joyram Guin
Journal: Chem Sci Date: 2018-07-02 Impact factor: 9.825

A new organocatalytic concept for asymmetric α-alkylation of aldehydes.

1. Cross-dehydrogenative coupling enables enantioselective access to CF₃-substituted all-carbon quaternary stereocenters.

2. Copper-Catalyzed Borylative Aromatization of p-Quinone Methides: Enantioselective Synthesis of Dibenzylic Boronates.

3. Organocatalytic one-pot 1,4-/1,6-/1,2-addition sequence for the stereocontrolled formation of six consecutive stereocenters.

4. Organocatalytic synthesis of chiral tetrasubstituted allenes from racemic propargylic alcohols.

5. In the Mists of a Fungal Metabolite: An Unexpected Reaction of 2,4,5-Trimethoxyphenylglyoxylic Acid.

6. Synthesis of (E,E)-Dienones and (E,E)-Dienals via Palladium-Catalyzed γ,δ-Dehydrogenation of Enones and Enals.

7. Enantio- and diastereoselective diarylmethylation of 1,3-dicarbonyl compounds.

8. Copper-catalyzed silylation of p-quinone methides: new entry to dibenzylic silanes.

9. Asymmetric intramolecular α-cyclopropanation of aldehydes using a donor/acceptor carbene mimetic.

10. N-Heterocyclic carbenes as chiral Brønsted base catalysts: a highly diastereo- and enantioselective 1,6-addition reaction.