Literature DB >> 11890765

Organocatalytic Michael cycloisomerization of bis(enones): the intramolecular Rauhut-Currier reaction.

Long-Cheng Wang1, Ana Liza Luis, Kyriacos Agapiou, Hye-Young Jang, Michael J Krische.   

Abstract

The utilization of enones as latent enolates enables regioselective enolate formation from chemically robust presursors. In this communication, we report a catalytic Michael cycloisomerization of bis(enones) under Morita-Baylis-Hillman conditions. Upon exposure to 10 mol % tributylphosphine, bis(enone) substrates afford both five- and six-membered ring products. Notably, unsymmetrical bis(enones) possessing sufficient steric or electronic bias yield single isomeric products.

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Year:  2002        PMID: 11890765     DOI: 10.1021/ja0121686

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


  18 in total

1.  Total synthesis of (-)-spinosyn A.

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2.  Phosphine-catalyzed [4 + 2] annulation: synthesis of cyclohexenes.

Authors:  Yang S Tran; Ohyun Kwon
Journal:  J Am Chem Soc       Date:  2007-10-03       Impact factor: 15.419

3.  Quasi-Biomimetic Ring Contraction Catalyzed by a Cysteine-Based Nucleophile: Total Synthesis of Sch-642305, Some Analogs and their Putative anti-HIV Activities.

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Review 4.  Quantum mechanical investigations of organocatalysis: mechanisms, reactivities, and selectivities.

Authors:  Paul Ha-Yeon Cheong; Claude Y Legault; Joann M Um; Nihan Çelebi-Ölçüm; K N Houk
Journal:  Chem Rev       Date:  2011-06-28       Impact factor: 60.622

5.  Phosphine-catalyzed [4+2] annulations of 2-alkylallenoates and olefins: synthesis of multisubstituted cyclohexenes.

Authors:  Yang S Tran; Tioga J Martin; Ohyun Kwon
Journal:  Chem Asian J       Date:  2011-07-07

6.  Phosphine-Catalyzed Intramolecular Cyclizations of α-Nitroethylallenoates Forming (Z)-Furanone Oximes.

Authors:  Qing-Fa Zhou; Kui Zhang; Lingchao Cai; Ohyun Kwon
Journal:  Org Lett       Date:  2016-05-27       Impact factor: 6.005

7.  N-Heterocyclic Carbene-Promoted Rauhut]Currier Reactions between Vinyl Sulfones and α,β-Unsaturated Aldehydes.

Authors:  Roxanne L Atienza; Karl A Scheidt
Journal:  Aust J Chem       Date:  2011-08-19       Impact factor: 1.321

8.  Intramolecular Baylis-Hillman and morita reactions using unsaturated thiol ester substrates containing enolizable aldehydes.

Authors:  Gary E Keck; Dennie S Welch
Journal:  Org Lett       Date:  2002-10-17       Impact factor: 6.005

9.  Lewis acid-catalyzed conjugate additions of silyloxyallenes: a selective solution to the intermolecular Rauhut-Currier problem.

Authors:  Troy E Reynolds; Michael S Binkley; Karl A Scheidt
Journal:  Org Lett       Date:  2008-05-14       Impact factor: 6.005

10.  A nucleophile-catalyzed cycloisomerization permits a concise synthesis of (+)-harziphilone.

Authors:  Lucy M Stark; Klaus Pekari; Erik J Sorensen
Journal:  Proc Natl Acad Sci U S A       Date:  2004-07-01       Impact factor: 11.205

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