Literature DB >> 25266984

Reversal of the regiochemistry in the rhodium-catalyzed [4+3] cycloaddition between vinyldiazoacetates and dienes.

Pablo E Guzmán1, Yajing Lian, Huw M L Davies.   

Abstract

A regio-, diastereo-, and enantioselective [4+3] cycloaddition between vinylcarbenes and dienes has been achieved using the dirhodium tetracarboxylate catalyst [Rh2(S-BTPCP)4]. This methodology provides facile access to 1,4-cycloheptadienes that are regioisomers of those formed from the tandem cyclopropanation/Cope rearrangement reaction of vinylcarbenes with dienes.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  carbenoids; cycloaddition; diazo compounds; rhodium; synthetic methods

Mesh：

Substances：

Year:  2014        PMID： 25266984      PMCID： PMC4608551          DOI： 10.1002/anie.201406440

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  22 in total

1.  Highly regio- and stereoselective dirhodium vinylcarbene induced nitrone cycloaddition with subsequent cascade carbenoid aromatic cycloaddition/N-O cleavage and rearrangement.

Authors:  Xiaochen Wang; Quentin M Abrahams; Peter Y Zavalij; Michael P Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-26       Impact factor: 15.336

Review 2.  Catalytic enantioselective Diels--Alder reactions: methods, mechanistic fundamentals, pathways, and applications.

Authors:  E J Corey
Journal:  Angew Chem Int Ed Engl       Date:  2002-05-17       Impact factor: 15.336

3.  On the mechanism and selectivity of the combined C-H activation/Cope rearrangement.

Authors:  Jørn H Hansen; Timothy M Gregg; Stephanie R Ovalles; Yajing Lian; Jochen Autschbach; Huw M L Davies
Journal:  J Am Chem Soc       Date:  2011-03-08       Impact factor: 15.419

4.  Alkynoate synthesis through the vinylogous reactivity of rhodium(II) carbenoids.

Authors:  Damien Valette; Yajing Lian; John P Haydek; Kenneth I Hardcastle; Huw M L Davies
Journal:  Angew Chem Int Ed Engl       Date:  2012-07-16       Impact factor: 15.336

5.  Design, synthesis, and reactivity of 1-hydrazinodienes for use in organic synthesis.

Authors:  Glenn M Sammis; Eric M Flamme; Hao Xie; Douglas M Ho; Erik J Sorensen
Journal:  J Am Chem Soc       Date:  2005-06-22       Impact factor: 15.419

6.  D2-symmetric dirhodium catalyst derived from a 1,2,2-triarylcyclopropanecarboxylate ligand: design, synthesis and application.

Authors:  Changming Qin; Vyacheslav Boyarskikh; Jørn H Hansen; Kenneth I Hardcastle; Djamaladdin G Musaev; Huw M L Davies
Journal:  J Am Chem Soc       Date:  2011-11-02       Impact factor: 15.419

7.  Rhodium carbenoid approach for introduction of 4-substituted (Z)-pent-2-enoates into sterically encumbered pyrroles and indoles.

Authors:  Yajing Lian; Huw M L Davies
Journal:  Org Lett       Date:  2010-03-05       Impact factor: 6.005

8.  Rhodium-catalyzed enantioselective vinylogous addition of enol ethers to vinyldiazoacetates.

Authors:  Austin G Smith; Huw M L Davies
Journal:  J Am Chem Soc       Date:  2012-10-29       Impact factor: 15.419

9.  Vinylogous reactivity of enol diazoacetates with donor-acceptor substituted hydrazones. Synthesis of substituted pyrazole derivatives.

Authors:  Xinfang Xu; Peter Y Zavalij; Wenhao Hu; Michael P Doyle
Journal:  J Org Chem       Date:  2013-01-24       Impact factor: 4.354

10.  Rhodium(II)- and copper(II)-catalyzed reactions of enol diazoacetates with nitrones: metal carbene versus Lewis acid directed pathways.

Authors:  Yu Qian; Xinfang Xu; Xiaochen Wang; Peter J Zavalij; Wenhao Hu; Michael P Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2012-05-04       Impact factor: 15.336
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  7 in total

Review 1.  Catalytic asymmetric cycloaddition reactions of enoldiazo compounds.

Authors:  Kostiantyn O Marichev; Michael P Doyle
Journal:  Org Biomol Chem       Date:  2019-04-24       Impact factor: 3.876

2.  Catalytic Enantio- and Diastereoselective Cyclopropanation of 2-Azadienes for the Synthesis of Aminocyclopropanes Bearing Quaternary Carbon Stereogenic Centers.

Authors:  Xinxin Shao; Steven J Malcolmson
Journal:  Org Lett       Date:  2019-08-29       Impact factor: 6.005

Review 3.  Cycloaddition reactions of enoldiazo compounds.

Authors:  Qing-Qing Cheng; Yongming Deng; Marianne Lankelma; Michael P Doyle
Journal:  Chem Soc Rev       Date:  2017-08-29       Impact factor: 54.564

4.  Lewis Acid Mediated Vinylogous Additions of Enol Nucleophiles into an α,β-Unsaturated Platinum Carbene.

Authors:  Paul A Allegretti; Khoi Huynh; Tarik J Ozumerzifon; Eric M Ferreira
Journal:  Org Lett       Date:  2015-12-14       Impact factor: 6.005

5.  Functionalizing the γ-Position of α-Diazo-β-ketoesters.

Authors:  Thu Q Nguyen; Maha Alqurafi; Cash Edwards; Pauline Nguyen; Jean Kim; Samuel Casco; Maricka Bennet; Christopher Chiang; Maureen Lohry; Melina Cox; Byron Meshram; Duyen Le; Eugene Kim; Snigdha Smriti; Peter Oelschlaeger; John D Buynak
Journal:  Tetrahedron Lett       Date:  2016-06-16       Impact factor: 2.415

6.  Dirhodium(II)-Catalyzed Annulation of Enoldiazoacetamides with α-Diazoketones: An Efficient and Highly Selective Approach to Fused and Bridged Ring Systems.

Authors:  Qing-Qing Cheng; Julietta Yedoyan; Hadi Arman; Michael P Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2016-03-23       Impact factor: 15.336

7.  Finding Opportunities from Surprises and Failures. Development of Rhodium-Stabilized Donor/Acceptor Carbenes and Their Application to Catalyst-Controlled C-H Functionalization.

Authors:  Huw M L Davies
Journal:  J Org Chem       Date:  2019-10-10       Impact factor: 4.354
  7 in total

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