Literature DB >> 24273133

The catalytic asymmetric α-benzylation of aldehydes.

Benjamin List1, Ilija Čorić, Oleksandr O Grygorenko, Philip S J Kaib, Igor Komarov, Anna Lee, Markus Leutzsch, Subhas Chandra Pan, Andrey V Tymtsunik, Manuel van Gemmeren.   

Abstract

The first aminocatalyzed α-alkylation of α-branched aldehydes with benzyl bromides as alkylating agents has been developed. Using a sterically demanding proline derived catalyst, racemic α-branched aldehydes are reacted with alkylating agents in a DYKAT process to give the corresponding α-alkylated aldehydes with quaternary stereogenic centers in good yields and high enantioselectivities.
Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  DYKATt; enamine catalysis; organocatalysis; α-alkylation; α-branched aldehydes

Year:  2013        PMID: 24273133     DOI: 10.1002/anie.201306037

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  6 in total

Review 1.  The ever-expanding role of asymmetric covalent organocatalysis in scalable, natural product synthesis.

Authors:  Mikail E Abbasov; Daniel Romo
Journal:  Nat Prod Rep       Date:  2014-10       Impact factor: 13.423

2.  Enantioselective α-Alkylation of Aldehydes by Photoredox Organocatalysis: Rapid Access to Pharmacophore Fragments from β-Cyanoaldehydes.

Authors:  Eric R Welin; Alexander A Warkentin; Jay C Conrad; David W C MacMillan
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-30       Impact factor: 15.336

3.  Synergistic Peptide and Gold Catalysis: Enantioselective Addition of Branched Aldehydes to Allenamides.

Authors:  Leo D M Nicholls; Helma Wennemers
Journal:  Chemistry       Date:  2021-10-13       Impact factor: 5.020

4.  A BINOL-phosphoric acid and metalloporphyrin derived chiral covalent organic framework for enantioselective α-benzylation of aldehydes.

Authors:  Hui-Chao Ma; Ya-Nan Sun; Gong-Jun Chen; Yu-Bin Dong
Journal:  Chem Sci       Date:  2022-01-14       Impact factor: 9.825

Review 5.  Synergistic Strategies in Aminocatalysis.

Authors:  Antonio Del Vecchio; Arianna Sinibaldi; Valeria Nori; Giuliana Giorgianni; Graziano Di Carmine; Fabio Pesciaioli
Journal:  Chemistry       Date:  2022-07-04       Impact factor: 5.020

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

Authors:  Chaosheng Luo; Zhen Wang; Yong Huang
Journal:  Nat Commun       Date:  2015-12-08       Impact factor: 14.919

  6 in total

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