Literature DB >> 17249775

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

Jian-Wu Xie1, Lei Yue, Wei Chen, Wei Du, Jin Zhu, Jin-Gen Deng, Ying-Chun Chen.   

Abstract

[reaction: see text] The highly enantioselective Michael addition of 1,3-cyclic dicarbonyl compounds to alpha,beta-unsaturated ketones was reported to be catalyzed by an organic primary amine derived from quinine. A chiral anticoagulant drug, (S)-warfarin, was directly prepared in 96% ee, and other related important adducts were also obtained in excellent enantioselectivity (89-99% ee).

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Year:  2007        PMID： 17249775     DOI： 10.1021/ol062718a

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


  14 in total

1.  Catalytic enantioselective peroxidation of alpha,beta-unsaturated ketones.

Authors:  Xiaojie Lu; Yan Liu; Bingfeng Sun; Brittany Cindric; Li Deng
Journal:  J Am Chem Soc       Date:  2008-06-05       Impact factor: 15.419

2.  Asymmetric aza-Michael reactions of alpha,beta-unsaturated ketones with bifunctional organic catalysts.

Authors:  Xiaojie Lu; Li Deng
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  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

4.  Warfarin glycosylation invokes a switch from anticoagulant to anticancer activity.

Authors:  Pauline Peltier-Pain; Shannon C Timmons; Agnès Grandemange; Etienne Benoit; Jon S Thorson
Journal:  ChemMedChem       Date:  2011-06-28       Impact factor: 3.466

5.  Enantioselective organocatalytic α-fluorination of cyclic ketones.

Authors:  Piotr Kwiatkowski; Teresa D Beeson; Jay C Conrad; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2011-01-19       Impact factor: 15.419

6.  Asymmetric approach toward chiral cyclohex-2-enones from anisoles via an enantioselective isomerization by a new chiral diamine catalyst.

Authors:  Jung Hwa Lee; Li Deng
Journal:  J Am Chem Soc       Date:  2012-10-22       Impact factor: 15.419

7.  Synthesis and catalytic properties of diverse chiral polyamines.

Authors:  Mindy Levine; Craig S Kenesky; Shengping Zheng; Jordan Quinn; Ronald Breslow
Journal:  Tetrahedron Lett       Date:  2008-09-29       Impact factor: 2.415

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

Authors:  Sanjib Gogoi; Cong-Gui Zhao; Derong Ding
Journal:  Org Lett       Date:  2009-06-04       Impact factor: 6.005

9.  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

10.  Bioinspired total synthesis of katsumadain A by organocatalytic enantioselective 1,4-conjugate addition.

Authors:  Yongguang Wang; Ruiyang Bao; Shengdian Huang; Yefeng Tang
Journal:  Beilstein J Org Chem       Date:  2013-08-06       Impact factor: 2.883
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