Literature DB >> 17691800

Organocatalytic and highly enantioselective direct alpha-amination of aromatic ketones.

Tian-Yu Liu1, Hai-Lei Cui, Yan Zhang, Kun Jiang, Wei Du, Zhao-Quan He, Ying-Chun Chen.   

Abstract

The first highly enantioselective direct alpha-amination of aryl ketones was reported to be catalyzed by organic primary amines derived from cinchona alkaloids. Excellent enantioselectivities (88-99% ee) have been achieved for a broad spectrum of aryl ketones. The presence of 4 A molecular sieves was of great assistance for the high conversions and enantiocontrol.

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Year:  2007        PMID： 17691800     DOI： 10.1021/ol701648x

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  10 in total

1.  Primary Amine-Catalyzed Biginelli Reaction for the Enantioselective Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones.

Authors:  Derong Ding; Cong-Gui Zhao
Journal:  European J Org Chem       Date:  2010-07-01

2.  Asymmetric aza-Michael reactions of alpha,beta-unsaturated ketones with bifunctional organic catalysts.

Authors:  Xiaojie Lu; Li Deng
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  Cinchona alkaloid catalyzed enantioselective amination of α,β-unsaturated ketones: an asymmetric approach to Δ2-pyrazolines.

Authors:  Nathaniel R Campbell; Bingfeng Sun; Ravi P Singh; Li Deng
Journal:  Adv Synth Catal       Date:  2011-11-01       Impact factor: 5.837

4.  Organocatalytic High Enantioselective Synthesis of β-Formyl-α-hydroxyphosphonates.

Authors:  Sandun Perera; Vijaya Kumar Naganaboina; Long Wang; Bin Zhang; Qunsheng Guo; Laxmidhar Rout; Cong-Gui Zhao
Journal:  Adv Synth Catal       Date:  2011-06-30       Impact factor: 5.837

5.  Organocatalyzed enantioselective aldol reaction of 1H-pyrrole-2,3-diones.

Authors:  Mayur Bhanushali; Cong-Gui Zhao
Journal:  Tetrahedron Lett       Date:  2011-11-19       Impact factor: 2.415

6.  Direct asymmetric amination of α-branched cyclic ketones catalyzed by a chiral phosphoric acid.

Authors:  Xiaoyu Yang; F Dean Toste
Journal:  J Am Chem Soc       Date:  2015-02-26       Impact factor: 15.419

7.  Highly enantioselective borane reduction of heteroaryl and heterocyclic ketoxime ethers catalyzed by novel spiroborate ester derived from diphenylvalinol: application to the synthesis of nicotine analogues.

Authors:  Kun Huang; Francisco G Merced; Margarita Ortiz-Marciales; Héctor J Meléndez; Wildeliz Correa; Melvin De Jesús
Journal:  J Org Chem       Date:  2008-05-01       Impact factor: 4.354

Review 8.  Organocatalyzed asymmetric alpha-oxidation, alpha-aminoxylation and alpha-amination of carbonyl compounds.

Authors:  Tirayut Vilaivan; Worawan Bhanthumnavin
Journal:  Molecules       Date:  2010-02-11       Impact factor: 4.411

9.  Enantioselective α-Amination Enabled by a BINAM-Derived Phase-Transfer Catalyst.

Authors:  H M Nelson; J S Patel; H P Shunatona; F D Toste
Journal:  Chem Sci       Date:  2015-01-01       Impact factor: 9.825

10.  Direct catalytic enantioselective amination of ketones for the formation of tri- and tetrasubstituted stereocenters.

Authors:  B M Trost; J S Tracy; T Saget
Journal:  Chem Sci       Date:  2018-02-14       Impact factor: 9.825
  10 in total

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