Literature DB >> 27983825

Frustrated Lewis Acid/Brønsted Base Catalysts for Direct Enantioselective α-Amination of Carbonyl Compounds.

Ming Shang1, Xiaoxu Wang1, Seung Moh Koo1, Jennifer Youn1, Jessica Z Chan1, Wenzhi Yao1, Brian T Hastings1, Masayuki Wasa1.   

Abstract

A method for enantioselective direct α-amination reaction catalyzed by a sterically "frustrated" Lewis acid/Brønsted base complex is disclosed. Cooperative functioning of the Lewis acid and Brønsted base components gives rise to in situ enolate generation from monocarbonyl compounds. Subsequent reaction with hydrogen-bond activated dialkyl azodicarboxylates delivers α-aminocarbonyl compounds in high enantiomeric purity.

Entities:  

Year:  2016        PMID： 27983825     DOI： 10.1021/jacs.6b11908

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


  7 in total

1.  Enantioselective Conia-Ene-Type Cyclizations of Alkynyl Ketones through Cooperative Action of B(C6F5)3, N-Alkylamine and a Zn-Based Catalyst.

Authors:  Min Cao; Ahmet Yesilcimen; Masayuki Wasa
Journal:  J Am Chem Soc       Date:  2019-02-27       Impact factor: 15.419

2.  Catalytic Deuterium Incorporation within Metabolically Stable β-Amino C-H Bonds of Drug Molecules.

Authors:  Yejin Chang; Ahmet Yesilcimen; Min Cao; Yuyang Zhang; Bochao Zhang; Jessica Z Chan; Masayuki Wasa
Journal:  J Am Chem Soc       Date:  2019-09-09       Impact factor: 15.419

3.  B(C6F5)3-Catalyzed α-Deuteration of Bioactive Carbonyl Compounds with D2O.

Authors:  Yejin Chang; Tanner Myers; Masayuki Wasa
Journal:  Adv Synth Catal       Date:  2019-11-26       Impact factor: 5.837

4.  B(C6F5)3-catalyzed dehydrogenative cyclization of N-tosylhydrazones and anilines via a Lewis adduct: a combined experimental and computational investigation.

Authors:  Murali Mohan Guru; Sriman De; Sayan Dutta; Debasis Koley; Biplab Maji
Journal:  Chem Sci       Date:  2019-07-05       Impact factor: 9.825

5.  Sequential Conia-ene-type cyclization and Negishi coupling by cooperative functions of B(C6F5)3, ZnI2, Pd(PPh3)4 and an amine.

Authors:  Min Cao; Ahmet Yesilcimen; Soumil Prasad; Jason Genova; Tanner Myers; Masayuki Wasa
Journal:  Org Biomol Chem       Date:  2020-09-23       Impact factor: 3.876

6.  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

7.  Enantioselective α-functionalizations of ketones via allylic substitution of silyl enol ethers.

Authors:  Zhi-Tao He; John F Hartwig
Journal:  Nat Chem       Date:  2018-11-19       Impact factor: 24.427
  7 in total

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