Literature DB >> 15771486

Bifunctional organocatalysts for enantioselective aza-Morita-Baylis-Hillman reaction.

Katsuya Matsui1, Shinobu Takizawa, Hiroaki Sasai.   

Abstract

The efficient and novel bifunctional organocatalyst for the enantioselective aza-Morita-Baylis-Hillman (aza-MBH) reaction has been established with (S)-3-(N-isopropyl-N-3-pyridinylaminomethyl)BINOL for the first time. The reaction proved to be deeply influenced by the position of the Lewis base attached to BINOL. The acid-base-mediated functionalities for the activation of the substrate and the fixing of conformation of the organocatalyst are harmoniously performed to promote the reaction with high enantiocontrol.

Entities:  

Year:  2005        PMID: 15771486     DOI: 10.1021/ja0500254

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


  8 in total

1.  Theory-Guided Design of Brønsted Acid-Assisted Phosphine Catalysis: Synthesis of Dihydropyrones from Aldehydes and Allenoates.

Authors:  Gardner S Creech; Xue-Feng Zhu; Branden Fonovic; Travis Dudding; Ohyun Kwon
Journal:  Tetrahedron       Date:  2008-07-14       Impact factor: 2.457

2.  Exploring the potential of diarylacetylenediols as hydrogen bonding catalysts.

Authors:  Yunus E Türkmen; Viresh H Rawal
Journal:  J Org Chem       Date:  2013-08-14       Impact factor: 4.354

3.  Intermolecular hydroamination of allenes with N-unsubstituted carbamates catalyzed by a gold(I) N-heterocyclic carbene complex.

Authors:  Robert E Kinder; Zhibin Zhang; Ross A Widenhoefer
Journal:  Org Lett       Date:  2008-06-21       Impact factor: 6.005

4.  Asymmetric catalytic aza-Morita-Baylis-Hillman reaction for the synthesis of 3-substituted-3-aminooxindoles with chiral quaternary carbon centers.

Authors:  Fang-Le Hu; Yin Wei; Min Shi; Suresh Pindi; Guigen Li
Journal:  Org Biomol Chem       Date:  2013-02-13       Impact factor: 3.876

5.  Novel bifunctional sulfonamides catalyze an enantioselective conjugate addition.

Authors:  Patrick G McGarraugh; Stacey E Brenner
Journal:  Tetrahedron       Date:  2009-01-10       Impact factor: 2.457

6.  Dynamic covalent organocatalysts discovered from catalytic systems through rapid deconvolution screening.

Authors:  Fredrik Schaufelberger; Olof Ramström
Journal:  Chemistry       Date:  2015-07-14       Impact factor: 5.236

Review 7.  Enantioselective, organocatalytic Morita-Baylis-Hillman and Aza-Morita-Baylis-Hillman reactions: stereochemical issues.

Authors:  Javier Mansilla; José M Saá
Journal:  Molecules       Date:  2010-02-01       Impact factor: 4.411

8.  Cu-catalyzed cyanomethylation of imines and α,β-alkenes with acetonitrile and its derivatives.

Authors:  Muhammad Siddique Ahmad; Atique Ahmad
Journal:  RSC Adv       Date:  2021-01-28       Impact factor: 3.361

  8 in total

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