Literature DB >> 16417358

Enantioselective nitroaldol reaction of alpha-ketoesters catalyzed by cinchona alkaloids.

Hongming Li1, Baomin Wang, Li Deng.   

Abstract

The development of highly enantioselective and general catalytic nitroaldol (Henry) reactions with ketones is a challenging yet desirable task in organic synthesis. In this communication, we report an asymmetric nitroaldol reaction with alpha-ketoesters catalyzed by a new C6'-OH cinchona alkaloid catalyst. This is the first highly efficient organocatalytic asymmetric Henry reaction with ketones. This reaction is operationally simple and affords high enantioselectivity as well as good to excellent yield for a broad range of alpha-ketoesters.

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Year:  2006        PMID： 16417358      PMCID： PMC3161415          DOI： 10.1021/ja057237l

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


  19 in total

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Authors:  Barry M Trost; Vince S C Yeh; Hisanako Ito; Nadine Bremeyer
Journal:  Org Lett       Date:  2002-08-08       Impact factor: 6.005

2.  A dinuclear Zn catalyst for the asymmetric nitroaldol (Henry) reaction.

Authors:  Barry M Trost; Vince S C Yeh
Journal:  Angew Chem Int Ed Engl       Date:  2002-03-01       Impact factor: 15.336

3.  Highly enantioselective thiourea-catalyzed nitro-Mannich reactions.

Authors:  Tehshik P Yoon; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2005-01-07       Impact factor: 15.336

4.  Catalytic enantioselective C-C bond forming conjugate additions with vinyl sulfones.

Authors:  Hongming Li; Jun Song; Xiaofeng Liu; Li Deng
Journal:  J Am Chem Soc       Date:  2005-06-29       Impact factor: 15.419

5.  Asymmetric Henry reaction catalyzed by C2-symmetric tridentate bis(oxazoline) and bis(thiazoline) complexes: metal-controlled reversal of enantioselectivity.

Authors:  Da-Ming Du; Shao-Feng Lu; Tao Fang; Jiaxi Xu
Journal:  J Org Chem       Date:  2005-04-29       Impact factor: 4.354

6.  Designer chiral quaternary ammonium bifluorides as an efficient catalyst for asymmetric nitroaldol reaction of silyl nitronates with aromatic aldehydes.

Authors:  Takashi Ooi; Kanae Doda; Keiji Maruoka
Journal:  J Am Chem Soc       Date:  2003-02-26       Impact factor: 15.419

7.  Highly enantioselective amination of alpha-substituted alpha-cyanoacetates with chiral catalysts accessible from both quinine and quinidine.

Authors:  Xiaofeng Liu; Hongming Li; Li Deng
Journal:  Org Lett       Date:  2005-01-20       Impact factor: 6.005

8.  Asymmetric catalytic aza-Henry reactions leading to 1,2-diamines and 1,2-diaminocarboxylic acids.

Authors:  Bernhard Westermann
Journal:  Angew Chem Int Ed Engl       Date:  2003-01-13       Impact factor: 15.336

9.  A new copper acetate-bis(oxazoline)-catalyzed, enantioselective Henry reaction.

Authors:  David A Evans; Daniel Seidel; Magnus Rueping; Hon Wai Lam; Jared T Shaw; C Wade Downey
Journal:  J Am Chem Soc       Date:  2003-10-22       Impact factor: 15.419

10.  Enantioselective aza-Henry reaction catalyzed by a bifunctional organocatalyst.

Authors:  Tomotaka Okino; Satoru Nakamura; Tomihiro Furukawa; Yoshiji Takemoto
Journal:  Org Lett       Date:  2004-02-19       Impact factor: 6.005
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  17 in total

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Journal:  J Am Chem Soc       Date:  2007-05-01       Impact factor: 15.419

2.  Synthesis of Chiral Nonracemic Tertiary α-Thio and α-Sulfonyl Acetic Esters via S(N)2 reactions of Tertiary Mesylates.

Authors:  Jimmie D Weaver; David K Morris; Jon A Tunge
Journal:  Synlett       Date:  2010-02-01       Impact factor: 2.454

3.  Three-component glycolate Michael reactions of enolates, silyl glyoxylates, and α,β-enones.

Authors:  Daniel C Schmitt; Ericka J Malow; Jeffrey S Johnson
Journal:  J Org Chem       Date:  2012-03-15       Impact factor: 4.354

4.  Asymmetric Friedel-crafts reaction of indoles with imines by an organic catalyst.

Authors:  Yong-Qiang Wang; Jun Song; Ran Hong; Hongming Li; Li Deng
Journal:  J Am Chem Soc       Date:  2006-06-28       Impact factor: 15.419

5.  The Mannich reaction of malonates with simple imines catalyzed by bifunctional cinchona alkaloids: enantioselective synthesis of beta-amino acids.

Authors:  Jun Song; Yi Wang; Li Deng
Journal:  J Am Chem Soc       Date:  2006-05-10       Impact factor: 15.419

6.  Highly Enantioselective Asymmetric Darzens Reactions with a Phase Transfer Catalyst.

Authors:  Yan Liu; Brian A Provencher; Keith J Bartleson; Li Deng
Journal:  Chem Sci       Date:  2011-07       Impact factor: 9.825

7.  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

8.  Catalytic enantioselective alkylation of substituted dioxanone enol ethers: ready access to Calpha-tetrasubstituted hydroxyketones, acids, and esters.

Authors:  Masaki Seto; Jennifer L Roizen; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

9.  Dynamic kinetic asymmetric transformations of β-stereogenic α-ketoesters by direct aldolization.

Authors:  Michael T Corbett; Jeffrey S Johnson
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-12       Impact factor: 15.336

10.  Asymmetric synthesis of diverse glycolic acid scaffolds via dynamic kinetic resolution of α-keto esters.

Authors:  Kimberly M Steward; Michael T Corbett; C Guy Goodman; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2012-11-27       Impact factor: 15.419
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