Literature DB >> 22893602

Cinchona-based primary amine catalysis in the asymmetric functionalization of carbonyl compounds.

Paolo Melchiorre1.   

Abstract

Asymmetric aminocatalysis exploits the potential of chiral primary and secondary amines to catalyze asymmetric reactions. It has greatly simplified the functionalization of carbonyl compounds while ensuring high enantioselectivity. Recent advances in cinchona-based primary amine catalysis have provided new synthetic opportunities and conceptual perspectives for successfully attacking major challenges in carbonyl compound chemistry, which traditional approaches have not been able to address. This Review outlines the historical context for the development of this catalyst class while charting the landmark discoveries and applications that have further expanded the synthetic potential of aminocatalysis.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Year:  2012        PMID: 22893602     DOI: 10.1002/anie.201109036

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


  27 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.  Switchable regioselectivity in amine-catalysed asymmetric cycloadditions.

Authors:  Zhi Zhou; Zhou-Xiang Wang; Yuan-Chun Zhou; Wei Xiao; Qin Ouyang; Wei Du; Ying-Chun Chen
Journal:  Nat Chem       Date:  2017-01-16       Impact factor: 24.427

3.  Synthesis of 9-amino(9-deoxy)epi cinchona alkaloids, general chiral organocatalysts for the stereoselective functionalization of carbonyl compounds.

Authors:  Carlo Cassani; Rafael Martín-Rapún; Elena Arceo; Fernando Bravo; Paolo Melchiorre
Journal:  Nat Protoc       Date:  2013-01-17       Impact factor: 13.491

4.  Organocatalytic stereoselective [8+2] and [6+4] cycloadditions.

Authors:  Rasmus Mose; Gert Preegel; Jesper Larsen; Sofie Jakobsen; Eva Høgh Iversen; Karl Anker Jørgensen
Journal:  Nat Chem       Date:  2016-12-19       Impact factor: 24.427

5.  Catalytic Isonitrile Insertions and Condensations Initiated by RNC-X Complexation.

Authors:  Suravi Chakrabarty; Shruti Choudhary; Arpit Doshi; Fa-Qiang Liu; Rishabh Mohan; Manasa P Ravindra; Dhruv Shah; Xun Yang; Fraser F Fleming
Journal:  Adv Synth Catal       Date:  2014-06-20       Impact factor: 5.837

6.  Origin of and a Solution for Uneven Efficiency by Cinchona Alkaloid-Derived, Pseudoenantiomeric Catalysts for Asymmetric Reactions.

Authors:  Bin Hu; Mark W Bezpalko; Chao Fei; Diane A Dickie; Bruce M Foxman; Li Deng
Journal:  J Am Chem Soc       Date:  2018-10-09       Impact factor: 15.419

7.  Enantioselective Michael addition of malonates to α,β-unsaturated ketones catalyzed by 1,2-diphenylethanediamine.

Authors:  Wei Wang; Ling Ye; Zhichuan Shi; Zhigang Zhao; Xuefeng Li
Journal:  RSC Adv       Date:  2018-12-12       Impact factor: 4.036

8.  Asymmetric fluorination of α-branched cyclohexanones enabled by a combination of chiral anion phase-transfer catalysis and enamine catalysis using protected amino acids.

Authors:  Xiaoyu Yang; Robert J Phipps; F Dean Toste
Journal:  J Am Chem Soc       Date:  2014-03-31       Impact factor: 15.419

9.  Asymmetric synthesis of highly functionalized tetrahydropyrans via a one-pot organocatalytic Michael/Henry/ketalization sequence.

Authors:  Robert Hahn; Gerhard Raabe; Dieter Enders
Journal:  Org Lett       Date:  2014-06-27       Impact factor: 6.005

10.  Primary-tertiary diamine-catalyzed Michael addition of ketones to isatylidenemalononitrile derivatives.

Authors:  Akshay Kumar; Swapandeep Singh Chimni
Journal:  Beilstein J Org Chem       Date:  2014-04-24       Impact factor: 2.883

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