Literature DB >> 21780842

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

Xiaodan Zhao1, Daniel A DiRocco, Tomislav Rovis.   

Abstract

An efficient enantioselective approach to form trans-γ-lactams in up to 99% yield, 93% ee, and >20/1 dr using unactivated imines has been developed. The cyclohexyl-substituted azolium and the weak base sodium o-chlorobenzoate are most suitable for this transformation. Notably, the process involves cooperative catalysis by an N-heterocyclic carbene and a Brønsted acid.

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Year:  2011        PMID： 21780842      PMCID： PMC3155423          DOI： 10.1021/ja205714g

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


  62 in total

1.  Salinosporamide A: a highly cytotoxic proteasome inhibitor from a novel microbial source, a marine bacterium of the new genus salinospora.

Authors:  Robert H Feling; Greg O Buchanan; Tracy J Mincer; Christopher A Kauffman; Paul R Jensen; William Fenical
Journal:  Angew Chem Int Ed Engl       Date:  2003-01-20       Impact factor: 15.336

2.  Discovering New Reactions with N-Heterocyclic Carbene Catalysis.

Authors:  Eric M Phillips; Audrey Chan; Karl A Scheidt
Journal:  Aldrichimica Acta       Date:  2009       Impact factor: 3.667

3.  Enantioselective, cyclopentene-forming annulations via NHC-catalyzed benzoin-oxy-cope reactions.

Authors:  Pei-Chen Chiang; Juthanat Kaeobamrung; Jeffrey W Bode
Journal:  J Am Chem Soc       Date:  2007-03-03       Impact factor: 15.419

Review 4.  Organocatalysis by N-heterocyclic carbenes.

Authors:  Dieter Enders; Oliver Niemeier; Alexander Henseler
Journal:  Chem Rev       Date:  2007-10-23       Impact factor: 60.622

5.  Hydrogen-bonding asymmetric metal catalysis with alpha-amino acids: a simple and tunable approach to high enantioinduction.

Authors:  Yingdong Lu; Tim C Johnstone; Bruce A Arndtsen
Journal:  J Am Chem Soc       Date:  2009-08-19       Impact factor: 15.419

6.  Catalytic asymmetric intermolecular Stetter reaction of enals with nitroalkenes: enhancement of catalytic efficiency through bifunctional additives.

Authors:  Daniel A DiRocco; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2011-06-16       Impact factor: 15.419

7.  Catalytic Synthesis of gamma-Lactams via direct annulations of enals and N-sulfonylimines.

Authors:  Ming He; Jeffrey W Bode
Journal:  Org Lett       Date:  2005-07-07       Impact factor: 6.005

8.  Catalytic asymmetric intermolecular Stetter reaction of glyoxamides with alkylidenemalonates.

Authors:  Qin Liu; Stéphane Perreault; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2008-10-04       Impact factor: 15.419

9.  Highly diastereoselective synthesis of beta-carboxy-gamma-lactams and their ethyl esters via Sc(OTf)(3)-catalyzed imino Mukaiyama-aldol type reaction of 2,5-bis(trimethylsilyloxy)furan with imines.

Authors:  Manat Pohmakotr; Nattawut Yotapan; Patoomratana Tuchinda; Chutima Kuhakarn; Vichai Reutrakul
Journal:  J Org Chem       Date:  2007-05-17       Impact factor: 4.354

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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  33 in total

1.  A Cooperative N-Heterocyclic Carbene/Palladium Catalysis System.

Authors:  Kun Liu; M Todd Hovey; Karl A Scheidt
Journal:  Chem Sci       Date:  2014-10-01       Impact factor: 9.825

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.  Enantioselective Synthesis of γ-Lactams by Lewis Base Catalyzed Sulfenoamidation of Alkenes.

Authors:  Jesse L Panger; Scott E Denmark
Journal:  Org Lett       Date:  2019-12-20       Impact factor: 6.005

4.  N-Heterocyclic carbene-catalyzed enantioselective annulations: a dual activation strategy for a formal [4+2] addition for dihydrocoumarins.

Authors:  Anna Lee; Karl A Scheidt
Journal:  Chem Commun (Camb)       Date:  2015-02-25       Impact factor: 6.222

5.  Switchable selectivity in an NHC-catalysed dearomatizing annulation reaction.

Authors:  Chang Guo; Mirco Fleige; Daniel Janssen-Müller; Constantin G Daniliuc; Frank Glorius
Journal:  Nat Chem       Date:  2015-08-31       Impact factor: 24.427

6.  Exploiting Acyl and Enol Azolium Intermediates via NHeterocyclic Carbene Catalyzed Reactions of Alpha-Reducible Aldehydes.

Authors:  Harit U Vora; Philip Wheeler; Tomislav Rovis
Journal:  Adv Synth Catal       Date:  2012-04-19       Impact factor: 5.837

7.  Asymmetric N-heterocyclic carbene catalyzed addition of enals to nitroalkenes: controlling stereochemistry via the homoenolate reactivity pathway to access δ-lactams.

Authors:  Nicholas A White; Daniel A DiRocco; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2013-05-28       Impact factor: 15.419

8.  Asymmetric homoenolate additions to acyl phosphonates through rational design of a tailored N-heterocyclic carbene catalyst.

Authors:  Ki Po Jang; Gerri E Hutson; Ryne C Johnston; Elizabeth O McCusker; Paul H-Y Cheong; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2013-12-17       Impact factor: 15.419

9.  Oxidatively Initiated NHC-Catalyzed Enantioselective Synthesis of 3,4-Disubstituted Cyclopentanones from Enals.

Authors:  Nicholas A White; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2015-08-10       Impact factor: 15.419

10.  Synthesis of a library of "lead-like" γ-lactams by a one pot, four-component reaction.

Authors:  Kevin S Martin; Michael J Di Maso; James C Fettinger; Jared T Shaw
Journal:  ACS Comb Sci       Date:  2013-06-12       Impact factor: 3.784
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