Literature DB >> 12553780

Diastereo- and enantioselective catalytic carbometallative aldol cycloreduction: tandem conjugate addition-aldol cyclization.

David F Cauble1, John D Gipson, Michael J Krische.   

Abstract

A catalytic diastereo- and enantioselective method for tandem conjugate addition-aldol cyclization is described. This methodology enables the formation of five- and six-membered ring products from aromatic and aliphatic mono-enone mono-ketone precursors. Notably, in a single manipulation, three contiguous stereogenic centers are created with high levels of relative and absolute stereocontrol.

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Year:  2003        PMID： 12553780     DOI： 10.1021/ja0211095

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


  11 in total

1.  Direct Copper-Free Domino Conjugate Addition-Cycloallylation using Organozinc Reagents.

Authors:  Venukrishnan Komanduri; Fernando Pedraza; Michael J Krische
Journal:  Adv Synth Catal       Date:  2008-07-07       Impact factor: 5.837

2.  Anionic four-electron donor-based palladacycles as catalysts for addition reactions of arylboronic acids with alpha,beta-unsaturated ketones, aldehydes, and alpha-ketoesters.

Authors:  Ping He; Yong Lu; Cheng-Guo Dong; Qiao-Sheng Hu
Journal:  Org Lett       Date:  2007-01-18       Impact factor: 6.005

3.  Sequential aldol condensation-transition metal-catalyzed addition reactions of aldehydes, methyl ketones, and arylboronic acids.

Authors:  Yuan-Xi Liao; Chun-Hui Xing; Matthew Israel; Qiao-Sheng Hu
Journal:  Org Lett       Date:  2011-03-18       Impact factor: 6.005

4.  Highly Stereoselective Cobalt(III)-Catalyzed Three-Component C-H Bond Addition Cascade.

Authors:  Jeffrey A Boerth; Joshua R Hummel; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-15       Impact factor: 15.336

5.  Pd(OAc)(2)-catalyzed domino reactions of 1,2-dihaloarenes and 2-haloaryl arenesulfonates with Grignard reagents: efficient synthesis of substituted fluorenes.

Authors:  Cheng-Guo Dong; Qiao-Sheng Hu
Journal:  Tetrahedron       Date:  2008-03-10       Impact factor: 2.457

6.  Tandem Aldol Condensation - Platinacycle-Catalyzed Addition Reactions of Aldehydes, Methyl Ketones and Arylboronic Acids.

Authors:  Yuan-Xi Liao; Qiao-Sheng Hu
Journal:  European J Org Chem       Date:  2012-09-05

7.  Desymmetrization of enone-diones via rhodium-catalyzed diastereo- and enantioselective tandem conjugate addition-aldol cyclization.

Authors:  Brian M Bocknack; Long-Cheng Wang; Michael J Krische
Journal:  Proc Natl Acad Sci U S A       Date:  2004-03-15       Impact factor: 11.205

8.  Nonenzymatic enantioselective synthesis of all-carbon quaternary centers through desymmetrization.

Authors:  Kimberly S Petersen
Journal:  Tetrahedron Lett       Date:  2015-11-25       Impact factor: 2.415

9.  Mechanistic studies on the catalytic cycle of rhodium-catalyzed asymmetric 1,4-addition of aryltitanate reagents to alpha,beta-unsaturated ketones.

Authors:  Norihito Tokunaga; Kazuhiro Yoshida; Tamio Hayashi
Journal:  Proc Natl Acad Sci U S A       Date:  2004-02-23       Impact factor: 11.205

10.  Rh(III)-Catalyzed Diastereoselective C-H Bond Addition/Cyclization Cascade of Enone Tethered Aldehydes.

Authors:  Jeffrey A Boerth; Jonathan A Ellman
Journal:  Chem Sci       Date:  2015-12-01       Impact factor: 9.825
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