Literature DB >> 19266504

Activation of hemiaminal ethers by chiral Brønsted acids for facile access to enantioselective two-carbon homologation using enecarbamates.

Masahiro Terada1, Kyoko Machioka, Keiichi Sorimachi.   

Abstract

An enriching experience: Chiral phosphoric acids have been used to catalyze the title transformation for aromatic and aliphatic hemiaminal ethers. The process affords the corresponding products in good to high enantioselectivity (see scheme; Boc = tert-butoxycarbonyl, G = aromatic group). The method enables facile access to highly enantioenriched 1,3-diamine derivatives.

Entities:  

Year:  2009        PMID： 19266504     DOI： 10.1002/anie.200805385

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


  10 in total

1.  Total synthesis of (+/-)- and (-)-actinophyllic acid.

Authors:  Connor L Martin; Larry E Overman; Jason M Rohde
Journal:  J Am Chem Soc       Date:  2010-04-07       Impact factor: 15.419

2.  Rapid catalyst screening by a continuous-flow microreactor interfaced with ultra-high-pressure liquid chromatography.

Authors:  Hui Fang; Qing Xiao; Fanghui Wu; Paul E Floreancig; Stephen G Weber
Journal:  J Org Chem       Date:  2010-08-20       Impact factor: 4.354

3.  Dynamic multi-component covalent assembly for the reversible binding of secondary alcohols and chirality sensing.

Authors:  Lei You; Jeffrey S Berman; Eric V Anslyn
Journal:  Nat Chem       Date:  2011-11-13       Impact factor: 24.427

4.  Bond cleavage, fragment modification and reassembly in enantioselective three-component reactions.

Authors:  Dan Zhang; Jun Zhou; Fei Xia; Zhenghui Kang; Wenhao Hu
Journal:  Nat Commun       Date:  2015-01-14       Impact factor: 14.919

5.  Selecting Chiral BINOL-Derived Phosphoric Acid Catalysts: General Model To Identify Steric Features Essential for Enantioselectivity.

Authors:  Jolene P Reid; Jonathan M Goodman
Journal:  Chemistry       Date:  2017-09-14       Impact factor: 5.236

6.  Iron-Catalyzed Meerwein Carbooxygenation of Electron-Rich Olefins: Studies with Styrenes, Vinyl Pyrrolidinone, and Vinyl Oxazolidinone.

Authors:  Edson Leonardo Scarpa de Souza; Carson Wiethan; Carlos Roque Duarte Correia
Journal:  ACS Omega       Date:  2019-10-29

7.  Non-Kolbe electrolysis of N-protected-α-amino acids: a standardized method for the synthesis of N-protected (1-methoxyalkyl)amines.

Authors:  A Walęcka-Kurczyk; J Adamek; K Walczak; M Michalak; A Październiok-Holewa
Journal:  RSC Adv       Date:  2022-01-12       Impact factor: 3.361

8.  Enantioselective Michael addition/iminium ion cyclization cascades of tryptamine-derived ureas.

Authors:  Isabelle Aillaud; David M Barber; Amber L Thompson; Darren J Dixon
Journal:  Org Lett       Date:  2013-05-30       Impact factor: 6.005

9.  Chiral Brønsted acid-catalyzed enantioselective Friedel-Crafts reaction of 2-methoxyfuran with aliphatic ketimines generated in situ.

Authors:  Azusa Kondoh; Yusuke Ota; Takazumi Komuro; Fuyuki Egawa; Kyohei Kanomata; Masahiro Terada
Journal:  Chem Sci       Date:  2015-10-30       Impact factor: 9.825

10.  Cu-catalyzed asymmetric addition of alcohols to β,γ-alkynyl-α-imino esters for the construction of linear chiral N,O-ketals.

Authors:  Cheng Sheng; Zheng Ling; Yicong Luo; Wanbin Zhang
Journal:  Nat Commun       Date:  2022-01-20       Impact factor: 14.919
  10 in total

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