Literature DB >> 19415906

Enantioselective synthesis of beta-(3-hydroxypyrazol-1-yl) ketones using an organocatalyzed Michael addition reaction.

Sanjib Gogoi1, Cong-Gui Zhao, Derong Ding.   

Abstract

Beta-(3-hydroxypyrazol-1-yl) ketones have been prepared in high yields and excellent enantioselectivities (94-98% ee) via a Michael addition reaction between 2-pyrazolin-5-ones and aliphatic acyclic alpha,beta-unsaturated ketones using 9-epi-9-amino-9-deoxyquinine as the catalyst. These results account for the first example of an aza-Michael addition of the ambident 2-pyrazolin-5-one anion to a Michael acceptor.

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Year:  2009        PMID： 19415906      PMCID： PMC2752151          DOI： 10.1021/ol900538q

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


  18 in total

1.  Highly enantioselective conjugate addition of nitromethane to chalcones using bifunctional cinchona organocatalysts.

Authors:  Benedek Vakulya; Szilárd Varga; Antal Csámpai; Tibor Soós
Journal:  Org Lett       Date:  2005-05-12       Impact factor: 6.005

Review 2.  Development of the renal glucose reabsorption inhibitors: a new mechanism for the pharmacotherapy of diabetes mellitus type 2.

Authors:  William N Washburn
Journal:  J Med Chem       Date:  2009-04-09       Impact factor: 7.446

3.  Control of four stereocenters in an organocatalytic domino double Michael reaction: efficient synthesis of multisubstituted cyclopentanes.

Authors:  Bin Tan; Zugui Shi; Pei Juan Chua; Guofu Zhong
Journal:  Org Lett       Date:  2008-07-11       Impact factor: 6.005

4.  Highly enantioselective michael addition of cyclic 1,3-dicarbonyl compounds to alpha,beta-unsaturated ketones.

Authors:  Jian-Wu Xie; Lei Yue; Wei Chen; Wei Du; Jin Zhu; Jin-Gen Deng; Ying-Chun Chen
Journal:  Org Lett       Date:  2007-02-01       Impact factor: 6.005

5.  Synthesis and biological evaluation of novel pyrazoles and indazoles as activators of the nitric oxide receptor, soluble guanylate cyclase.

Authors:  D L Selwood; D G Brummell; J Budworth; G E Burtin; R O Campbell; S S Chana; I G Charles; P A Fernandez; R C Glen; M C Goggin; A J Hobbs; M R Kling; Q Liu; D J Madge; S Meillerais; K L Powell; K Reynolds; G D Spacey; J N Stables; M A Tatlock; K A Wheeler; G Wishart; C K Woo
Journal:  J Med Chem       Date:  2001-01-04       Impact factor: 7.446

6.  Catalytic asymmetric hydroperoxidation of alpha,beta-unsaturated ketones: an approach to enantiopure peroxyhemiketals, epoxides, and aldols.

Authors:  Corinna M Reisinger; Xingwang Wang; Benjamin List
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

7.  Remogliflozin etabonate, in a novel category of selective low-affinity sodium glucose cotransporter (SGLT2) inhibitors, exhibits antidiabetic efficacy in rodent models.

Authors:  Yoshikazu Fujimori; Kenji Katsuno; Ikumi Nakashima; Yukiko Ishikawa-Takemura; Hideki Fujikura; Masayuki Isaji
Journal:  J Pharmacol Exp Ther       Date:  2008-06-26       Impact factor: 4.030

Review 8.  Cancer treatment-induced oral mucositis.

Authors:  Daniela Alterio; Barbara Alicja Jereczek-Fossa; Maria Rosaria Fiore; Gaia Piperno; Mohssen Ansarin; Roberto Orecchia
Journal:  Anticancer Res       Date:  2007 Mar-Apr       Impact factor: 2.480

9.  Strain-release electrophilic activation via E-cycloalkenones.

Authors:  Joseph Moran; Peter Dornan; André M Beauchemin
Journal:  Org Lett       Date:  2007-09-05       Impact factor: 6.005

10.  Organocatalyzed enantioselective synthesis of 6-amino-5-cyanodihydropyrano[2,3-c]pyrazoles.

Authors:  Sanjib Gogoi; Cong-Gui Zhao
Journal:  Tetrahedron Lett       Date:  2009-05-13       Impact factor: 2.415
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  8 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.  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

3.  Bifunctional cinchona alkaloid-squaramide-catalyzed highly enantioselective aza-Michael addition of indolines to α,β-unsaturated ketones.

Authors:  Arun K Ghosh; Bing Zhou
Journal:  Tetrahedron Lett       Date:  2013-07-03       Impact factor: 2.415

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.  Streocontrolled construction of six vicinal stereogenic centers on spiropyrazolones via organocascade Michael/Michael/1,2-addition reactions.

Authors:  Pankaj Chauhan; Suruchi Mahajan; Charles C J Loh; Gerhard Raabe; Dieter Enders
Journal:  Org Lett       Date:  2014-05-19       Impact factor: 6.005

7.  Metal-mediated aminocatalysis provides mild conditions: Enantioselective Michael addition mediated by primary amino catalysts and alkali-metal ions.

Authors:  Matthias Leven; Jörg M Neudörfl; Bernd Goldfuss
Journal:  Beilstein J Org Chem       Date:  2013-01-23       Impact factor: 2.883

8.  5-Methyl-1-[(4-methyl-phen-yl)sulfon-yl]-1H-pyrazol-3-yl 4-methyl-benzene-sulfonate.

Authors:  Shahzad Murtaza; Naghmana Kausar; M Nawaz Tahir; Javaria Tariq; Samaira Bibi
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-06-23
  8 in total

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