Literature DB >> 19492394

Alpha-chiral acetylenes having an all-carbon quaternary center: phase transfer catalyzed enantioselective alpha alkylation of alpha-alkyl-alpha-alkynyl esters.

Takuya Hashimoto1, Kazuki Sakata, Keiji Maruoka.   

Abstract

Going through the phases: The title reaction was found to proceed by an initial base-mediated isomerization to allenyl esters and subsequent phase transfer catalyzed alkylation at the alpha position of the ester (see scheme).

Entities:  

Year:  2009        PMID： 19492394     DOI： 10.1002/anie.200901977

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


  5 in total

1.  Catalytic synthesis of nonracemic azaproline derivatives by cyclization of β-alkynyl hydrazines under kinetic resolution conditions.

Authors:  Pradip Maity; Salvatore D Lepore
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-15       Impact factor: 15.336

2.  Diversification reactions of γ-silyl allenyl esters: selective conversion to all-carbon quaternary centers and γ-allene dicarbinols.

Authors:  Susovan Jana; Animesh Roy; Salvatore D Lepore
Journal:  Chem Commun (Camb)       Date:  2017-05-04       Impact factor: 6.222

3.  Phase-transfer-catalysed asymmetric synthesis of tetrasubstituted allenes.

Authors:  Takuya Hashimoto; Kazuki Sakata; Fumiko Tamakuni; Mark J Dutton; Keiji Maruoka
Journal:  Nat Chem       Date:  2013-02-10       Impact factor: 24.427

4.  CuH-Catalyzed Regio- and Enantioselective Hydrocarboxylation of Allenes: Toward Carboxylic Acids with Acyclic Quaternary Centers.

Authors:  Sheng Feng; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2021-03-24       Impact factor: 15.419

5.  Asymmetric construction of acyclic quaternary stereocenters via direct enantioselective additions of α-alkynyl ketones to allenamides.

Authors:  Jiawen Wang; Faqian He; Xiaoyu Yang
Journal:  Nat Commun       Date:  2021-11-18       Impact factor: 14.919
  5 in total

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