Literature DB >> 21391673

N-Heterocyclic carbene-catalyzed (4+2) cycloaddition/decarboxylation of silyl dienol ethers with α,β-unsaturated acid fluorides.

Sarah J Ryan1, Lisa Candish, David W Lupton.   

Abstract

Herein we report the first all-carbon N-heterocyclic carbene-catalyzed (4 + 2) cycloaddition. The reaction proceeds with α,β-unsaturated acid fluorides and silyl dienol ethers and produces 1,3-cyclohexadienes with complete diastereocontrol (dr >20:1) while demonstrating a new type of reaction cascade exploiting α,β-unsaturated acyl azoliums.
© 2011 American Chemical Society

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Year:  2011        PMID： 21391673     DOI： 10.1021/ja111067j

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


  19 in total

Review 1.  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

2.  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

3.  Arenophile-Mediated Dearomative Reduction.

Authors:  Mikiko Okumura; Stephanie M Nakamata Huynh; Jola Pospech; David Sarlah
Journal:  Angew Chem Int Ed Engl       Date:  2016-11-23       Impact factor: 15.336

4.  Sensitive and Accurate 13C Kinetic Isotope Effect Measurements Enabled by Polarization Transfer.

Authors:  Eugene E Kwan; Yongho Park; Harrison A Besser; Thayer L Anderson; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2016-12-29       Impact factor: 15.419

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.  Enantioselective acylation of silyl ketene acetals through fluoride anion-binding catalysis.

Authors:  James A Birrell; Jean-Nicolas Desrosiers; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2011-08-10       Impact factor: 15.419

7.  Chiral N-Heterocyclic Carbene Catalyzed Annulations of Enals and Ynals with Stable Enols: A Highly Enantioselective Coates-Claisen Rearrangement.

Authors:  Jessada Mahatthananchai; Juthanat Kaeobamrung; Jeffrey W Bode
Journal:  ACS Catal       Date:  2012-02-29       Impact factor: 13.084

8.  An N-heterocyclic carbene/Lewis acid strategy for the stereoselective synthesis of spirooxindole lactones.

Authors:  Julien Dugal-Tessier; Elizabeth A O'Bryan; Thomas B H Schroeder; Daniel T Cohen; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-04       Impact factor: 15.336

Review 9.  Asymmetric Organocatalysis: The Emerging Utility of α,β-Unsaturated Acylammonium Salts.

Authors:  Sreekumar Vellalath; Daniel Romo
Journal:  Angew Chem Int Ed Engl       Date:  2016-09-21       Impact factor: 15.336

10.  A Computational Study of the Origin of Stereoinduction in NHC-Catalyzed Annulation Reactions of α,β-Unsaturated Acyl Azoliums.

Authors:  Eirik Lyngvi; Jeffrey W Bode; Franziska Schoenebeck
Journal:  Chem Sci       Date:  2012-03-01       Impact factor: 9.825
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