Literature DB >> 21927711

Enamine/Carbene Cascade Catalysis in the Diastereo- and Enantioselective Synthesis of Functionalized Cyclopentanones.

Kerem E Ozboya1, Tomislav Rovis.   

Abstract

Herein we report an enantioselective synthesis of complex cyclopentanones using aliphatic aldehydes and activated enones. With the combination of a chiral secondary amine and a chiral triazolium catalyst, high diastereoselectivity and excellent enantioselectivity can be achieved. We present evidence of a clear cooperative effect when these two catalysts are present simultaneously in the system.

Entities:  

Year:  2011        PMID: 21927711      PMCID: PMC3173771          DOI: 10.1039/C1SC00175B

Source DB:  PubMed          Journal:  Chem Sci        ISSN: 2041-6520            Impact factor:   9.825


  41 in total

1.  Catalytic asymmetric oxa-Michael-Michael cascade for facile construction of chiral chromans via an aminal intermediate.

Authors:  Liansuo Zu; Shilei Zhang; Hexin Xie; Wei Wang
Journal:  Org Lett       Date:  2009-04-02       Impact factor: 6.005

2.  Targeting structural and stereochemical complexity by organocascade catalysis: construction of spirocyclic oxindoles having multiple stereocenters.

Authors:  Giorgio Bencivenni; Li-Yuan Wu; Andrea Mazzanti; Berardino Giannichi; Fabio Pesciaioli; Mao-Ping Song; Giuseppe Bartoli; Paolo Melchiorre
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

3.  The catalytic asymmetric Knoevenagel condensation.

Authors:  Anna Lee; Anna Michrowska; Sarah Sulzer-Mosse; Benjamin List
Journal:  Angew Chem Int Ed Engl       Date:  2011-01-20       Impact factor: 15.336

4.  Enantioselective organo-cascade catalysis.

Authors:  Yong Huang; Abbas M Walji; Catharine H Larsen; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2005-11-02       Impact factor: 15.419

5.  "One-pot" access to 4H-chromenes with formation of a chiral quaternary stereogenic center by a highly enantioselective iminium-allenamine involved oxa-Michael-aldol cascade.

Authors:  Chunliang Liu; Xinshuai Zhang; Rui Wang; Wei Wang
Journal:  Org Lett       Date:  2010-11-05       Impact factor: 6.005

6.  Organocatalytic enantioselective conjugate additions to enones.

Authors:  Jian Wang; Hao Li; Liansuo Zu; Wei Jiang; Hexin Xie; Wenhu Duan; Wei Wang
Journal:  J Am Chem Soc       Date:  2006-10-04       Impact factor: 15.419

7.  Catalytic intramolecular crossed aldehyde--ketone benzoin reactions: a novel synthesis of functionalized preanthraquinones.

Authors:  Yoshifumi Hachisu; Jeffrey W Bode; Keisuke Suzuki
Journal:  J Am Chem Soc       Date:  2003-07-16       Impact factor: 15.419

8.  Multicatalytic synthesis of complex tetrahydrofurans involving bismuth(III) triflate catalyzed intramolecular hydroalkoxylation of unactivated olefins.

Authors:  Brendan D Kelly; Julia M Allen; Rachel E Tundel; Tristan H Lambert
Journal:  Org Lett       Date:  2009-03-19       Impact factor: 6.005

9.  Organocatalytic Michael addition of aldehydes to gamma-keto-alpha,beta-unsaturated esters. an efficient entry to versatile chiral building blocks.

Authors:  Jing Wang; Anqi Ma; Dawei Ma
Journal:  Org Lett       Date:  2008-12-04       Impact factor: 6.005

10.  Cooperative catalysis by carbenes and Lewis acids in a highly stereoselective route to gamma-lactams.

Authors:  Dustin E A Raup; Benoit Cardinal-David; Dane Holte; Karl A Scheidt
Journal:  Nat Chem       Date:  2010-07-18       Impact factor: 24.427

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  11 in total

1.  An asymmetric synthesis of 1,2,4-trioxane anticancer agents via desymmetrization of peroxyquinols through a Brønsted acid catalysis cascade.

Authors:  David M Rubush; Michelle A Morges; Barbara J Rose; Douglas H Thamm; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2012-08-07       Impact factor: 15.419

Review 2.  Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.

Authors:  Darrin M Flanigan; Fedor Romanov-Michailidis; Nicholas A White; Tomislav Rovis
Journal:  Chem Rev       Date:  2015-05-20       Impact factor: 60.622

3.  N-Heterocyclic Carbene and Chiral Brønsted Acid Cooperative Catalysis for a Highly Enantioselective [4+2] Annulation.

Authors:  Dian-Feng Chen; Tomislav Rovis
Journal:  Synthesis (Stuttg)       Date:  2016-11-18       Impact factor: 3.157

4.  Catalytic dynamic kinetic resolutions with N-heterocyclic carbenes: asymmetric synthesis of highly substituted β-lactones.

Authors:  Daniel T Cohen; Chad C Eichman; Eric M Phillips; Emily R Zarefsky; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2012-06-14       Impact factor: 15.336

5.  Catalytic Kinetic Resolution of a Dynamic Racemate: Highly Stereoselective β-Lactone Formation by N-Heterocyclic Carbene Catalysis.

Authors:  Ryne C Johnston; Daniel T Cohen; Chad C Eichman; Karl A Scheidt; Paul Ha-Yeon Cheong
Journal:  Chem Sci       Date:  2014-05-01       Impact factor: 9.825

6.  N-heterocyclic carbene and Brønsted acid cooperative catalysis: asymmetric synthesis of trans-γ-lactams.

Authors:  Xiaodan Zhao; Daniel A DiRocco; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2011-07-25       Impact factor: 15.419

7.  Cooperative Lewis acid/N-heterocyclic carbene catalysis.

Authors:  Daniel T Cohen; Karl A Scheidt
Journal:  Chem Sci       Date:  2012-01-01       Impact factor: 9.825

8.  Catalytic asymmetric cross-aza-benzoin reactions of aliphatic aldehydes with N-Boc-protected imines.

Authors:  Daniel A DiRocco; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2012-05-04       Impact factor: 15.336

9.  SNAr-Derived Decomposition By-products Involving Pentafluorophenyl Triazolium Carbenes.

Authors:  Xiaodan Zhao; Garrett S Glover; Kevin M Oberg; Derek M Dalton; Tomislav Rovis
Journal:  Synlett       Date:  2013-06-17       Impact factor: 2.454

10.  Evolution of catalytic stereoselective olefin metathesis: from ancillary transformation to purveyor of stereochemical identity.

Authors:  Amir H Hoveyda
Journal:  J Org Chem       Date:  2014-04-10       Impact factor: 4.354

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