Literature DB >> 21366293

N-(heteroarenesulfonyl)prolinamides-catalyzed aldol reaction between acetone and aryl trihalomethyl ketones.

Noriyuki Hara1, Ryota Tamura, Yasuhiro Funahashi, Shuichi Nakamura.   

Abstract

Enantiomerically enriched trihalomethyl-substituted alcohols having a quaternary chiral carbon center can be prepared by the catalytic enantioselective cross-aldol reaction of acetone with trihalomethyl ketones by using N-(8-quinolinesulfonyl)prolinamide as an organocatalyst. The MO calculations elucidate that the hydrogen bonding between the sulfonimide proton and the 8-quinolyl nitrogen atom plays an important role in exerting the enantioselectivity of the reaction.

Entities:  

Year:  2011        PMID： 21366293     DOI： 10.1021/ol2001039

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


  9 in total

1.  Catalytic Enantioselective Addition of an Allyl Group to Ketones Containing a Tri-, a Di-, or a Monohalomethyl Moiety. Stereochemical Control Based on Distinctive Electronic and Steric Attributes of C-Cl, C-Br, and C-F Bonds.

Authors:  Diana C Fager; KyungA Lee; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2019-09-25       Impact factor: 15.419

2.  Asymmetric vinylogous aldol addition of alkylidene oxindoles on trifluoromethyl-α,β-unsaturated ketones.

Authors:  Simone Crotti; Giada Belletti; Nicola Di Iorio; Emanuela Marotta; Andrea Mazzanti; Paolo Righi; Giorgio Bencivenni
Journal:  RSC Adv       Date:  2018-09-28       Impact factor: 4.036

3.  Asymmetric synthesis of trifluoromethylated amines via catalytic enantioselective isomerization of imines.

Authors:  Yongwei Wu; Li Deng
Journal:  J Am Chem Soc       Date:  2012-08-23       Impact factor: 15.419

4.  Strategies for the Catalytic Enantioselective Synthesis of α-Trifluoromethyl Amines.

Authors:  Chibueze I Onyeagusi; Steven J Malcolmson
Journal:  ACS Catal       Date:  2020-10-12       Impact factor: 13.084

5.  Regio- and Enantioselective Synthesis of Trifluoromethyl-Substituted Homoallylic α-Tertiary NH2 -Amines by Reactions Facilitated by a Threonine-Based Boron-Containing Catalyst.

Authors:  Diana C Fager; Ryan J Morrison; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2020-05-08       Impact factor: 15.336

6.  NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides.

Authors:  Alyn T Davies; Mark D Greenhalgh; Alexandra M Z Slawin; Andrew D Smith
Journal:  Beilstein J Org Chem       Date:  2020-06-30       Impact factor: 2.883

7.  Construction of chiral α-tert-amine scaffolds via amine-catalyzed asymmetric Mannich reactions of alkyl-substituted ketimines.

Authors:  Chihiro Homma; Aika Takeshima; Taichi Kano; Keiji Maruoka
Journal:  Chem Sci       Date:  2020-11-27       Impact factor: 9.825

8.  Chiral Brønsted acid-catalyzed intramolecular SN2' reaction for enantioselective construction of a quaternary stereogenic center.

Authors:  Masahiro Shimizu; Jun Kikuchi; Azusa Kondoh; Masahiro Terada
Journal:  Chem Sci       Date:  2018-06-05       Impact factor: 9.825

9.  Development of copper-catalyzed enantioselective decarboxylative aldolization for the preparation of perfluorinated 1,3,5-triols featuring supramolecular recognition properties.

Authors:  Céline Sperandio; Jean Rodriguez; Adrien Quintard
Journal:  Chem Sci       Date:  2019-12-27       Impact factor: 9.825
  9 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.