Literature DB >> 19199770

Highly enantioselective hydrogenation of enamides catalyzed by chiral phosphoric acids.

Guilong Li1, Jon C Antilla.   

Abstract

A highly enantioselective hydrogenation of enamides catalyzed by a dual chiral-achiral acid system was developed. By employing a substoichiometric amount of a chiral phosphoric acid and acetic acid, catalyst loadings as low as 1 mol % of the chiral catalyst were sufficient to provide excellent yield and enantioselectivity of the reduction product.

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Year:  2009        PMID： 19199770      PMCID： PMC2765520          DOI： 10.1021/ol802860u

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


  50 in total

1.  A powerful Brønsted acid catalyst for the organocatalytic asymmetric transfer hydrogenation of imines.

Authors:  Sebastian Hoffmann; Abdul Majeed Seayad; Benjamin List
Journal:  Angew Chem Int Ed Engl       Date:  2005-12-01       Impact factor: 15.336

Review 2.  High-throughput and parallel screening methods in asymmetric hydrogenation.

Authors:  Christoph Jäkel; Rocco Paciello
Journal:  Chem Rev       Date:  2006-07       Impact factor: 60.622

3.  Chiral phosphoric acids: powerful organocatalysts for asymmetric addition reactions to imines.

Authors:  Stephen J Connon
Journal:  Angew Chem Int Ed Engl       Date:  2006-06-12       Impact factor: 15.336

4.  Cooperative coexistence: effective interplay of two Brønsted acids in the asymmetric synthesis of isoquinuclidines.

Authors:  Magnus Rueping; Cengiz Azap
Journal:  Angew Chem Int Ed Engl       Date:  2006-11-27       Impact factor: 15.336

Review 5.  Asymmetric organocatalytic reductions mediated by dihydropyridines.

Authors:  Stephen J Connon
Journal:  Org Biomol Chem       Date:  2007-09-11       Impact factor: 3.876

6.  Organocatalytic asymmetric three-component cyclization of cinnamaldehydes and primary amines with 1,3-dicarbonyl compounds: straightforward access to enantiomerically enriched dihydropyridines.

Authors:  Jun Jiang; Jie Yu; Xi-Xi Sun; Qin-Quan Rao; Liu-Zhu Gong
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

7.  Highly enantioselective organocatalytic carbonyl-ene reaction with strongly acidic, chiral Brønsted acids as efficient catalysts.

Authors:  Magnus Rueping; Thomas Theissmann; Alexander Kuenkel; René M Koenigs
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

8.  A highly enantioselective Brønsted acid catalyzed reaction cascade.

Authors:  Magnus Rueping; Andrey P Antonchick
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

9.  Asymmetric organocatalytic three-component 1,3-dipolar cycloaddition: control of stereochemistry via a chiral Brønsted acid activated dipole.

Authors:  Xiao-Hua Chen; Wen-Quan Zhang; Liu-Zhu Gong
Journal:  J Am Chem Soc       Date:  2008-04-03       Impact factor: 15.419

10.  Asymmetric transfer hydrogenation of beta,gamma-alkynyl alpha-imino esters by a Brønsted acid.

Authors:  Qiang Kang; Zhuo-An Zhao; Shu-Li You
Journal:  Org Lett       Date:  2008-04-18       Impact factor: 6.005
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  9 in total

1.  Single-operation deracemization of 3H-indolines and tetrahydroquinolines enabled by phase separation.

Authors:  Aaron D Lackner; Andrew V Samant; F Dean Toste
Journal:  J Am Chem Soc       Date:  2013-09-11       Impact factor: 15.419

2.  N-triflylthiophosphoramide catalyzed enantioselective Mukaiyama aldol reaction of aldehydes with silyl enol ethers of ketones.

Authors:  Cheol Hong Cheon; Hisashi Yamamoto
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

Review 3.  Alkynoates as Versatile and Powerful Chemical Tools for the Rapid Assembly of Diverse Heterocycles under Transition-Metal Catalysis: Recent Developments and Challenges.

Authors:  Imtiaz Khan; Aliya Ibrar; Sumera Zaib
Journal:  Top Curr Chem (Cham)       Date:  2021-01-05

4.  Rapid catalyst screening by a continuous-flow microreactor interfaced with ultra-high-pressure liquid chromatography.

Authors:  Hui Fang; Qing Xiao; Fanghui Wu; Paul E Floreancig; Stephen G Weber
Journal:  J Org Chem       Date:  2010-08-20       Impact factor: 4.354

5.  Divergent Stereoselectivity in Phosphothreonine (pThr)-Catalyzed Reductive Aminations of 3-Amidocyclohexanones.

Authors:  Christopher R Shugrue; Aaron L Featherston; Rachel M Lackner; Angela Lin; Scott J Miller
Journal:  J Org Chem       Date:  2018-04-05       Impact factor: 4.354

6.  Asymmetric synthesis of nonracemic primary amines via spiroborate-catalyzed reduction of pure (E)- and (Z)-O-benzyloximes: applications toward the synthesis of calcimimetic agents.

Authors:  Wenhua Ou; Sandraliz Espinosa; Héctor J Meléndez; Silvia M Farré; Jaime L Alvarez; Valerie Torres; Ileanne Martínez; Kiara M Santiago; Margarita Ortiz-Marciales
Journal:  J Org Chem       Date:  2013-05-13       Impact factor: 4.354

7.  Divergent synthesis of dual 1,4-dihydropyridines with different substituted patterns from enaminones and aldehydes through domino reactions.

Authors:  Fu-Jun Liu; Tian-Tian Sun; Yun-Gang Yang; Chao Huang; Xue-Bing Chen
Journal:  RSC Adv       Date:  2018-04-03       Impact factor: 3.361

8.  Selecting Chiral BINOL-Derived Phosphoric Acid Catalysts: General Model To Identify Steric Features Essential for Enantioselectivity.

Authors:  Jolene P Reid; Jonathan M Goodman
Journal:  Chemistry       Date:  2017-09-14       Impact factor: 5.236

9.  Chiral Phosphoric Acid Catalyzed Conversion of Epoxides into Thiiranes: Mechanism, Stereochemical Model, and New Catalyst Design.

Authors:  Meng Duan; Christian David Díaz-Oviedo; Yang Zhou; Xiangyang Chen; Peiyuan Yu; Benjamin List; Kendall N Houk; Yu Lan
Journal:  Angew Chem Int Ed Engl       Date:  2022-01-14       Impact factor: 16.823
  9 in total

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