Literature DB >> 22945294

Synthesis of tetrahydropyridazines by a metal-carbene-directed enantioselective vinylogous N-H insertion/Lewis acid-catalyzed diastereoselective Mannich addition.

Xinfang Xu1, Peter Y Zavalij, Michael P Doyle.   

Abstract

A versatile cascade of reactions, triggered by Rh(II)-catalyzed diazo decomposition followed by a vinylogous N-H insertion/Lewis acid catalyzed Mannich addition, that produces highly substituted 1,2,3,6-tetrahydropyridazines in up to 97 % ee with high yield and diastereocontrol has been developed.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID： 22945294      PMCID： PMC3517037          DOI： 10.1002/anie.201203962

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


  36 in total

1.  Asymmetric N-H insertion reaction cooperatively catalyzed by rhodium and chiral spiro phosphoric acids.

Authors:  Bin Xu; Shou-Fei Zhu; Xiu-Lan Xie; Jun-Jie Shen; Qi-Lin Zhou
Journal:  Angew Chem Int Ed Engl       Date:  2011-10-04       Impact factor: 15.336

2.  Diastereo- and enantioselective gold(I)-catalyzed intermolecular tandem cyclization/[3+3]cycloadditions of 2-(1-alkynyl)-2-alken-1-ones with nitrones.

Authors:  Feng Liu; Deyun Qian; Lei Li; Xiaoli Zhao; Junliang Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2010-09-03       Impact factor: 15.336

3.  Total synthesis of chloptosin.

Authors:  Alexander J Oelke; David J France; Tatjana Hofmann; Georg Wuitschik; Steven V Ley
Journal:  Angew Chem Int Ed Engl       Date:  2010-08-16       Impact factor: 15.336

4.  Catalytic enantioselective cross-Mannich reaction of aldehydes.

Authors:  Maria Manuel B Marques
Journal:  Angew Chem Int Ed Engl       Date:  2006-01-09       Impact factor: 15.336

5.  Copper-catalyzed asymmetric N-H insertion reactions: couplings of diazo compounds with carbamates to generate alpha-amino acids.

Authors:  Elaine C Lee; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2007-09-18       Impact factor: 15.419

Review 6.  N-acylhydrazones as versatile electrophiles for the synthesis of nitrogen-containing compounds.

Authors:  Masaharu Sugiura; Shū Kobayashi
Journal:  Angew Chem Int Ed Engl       Date:  2005-08-19       Impact factor: 15.336

7.  Enantioselective organocatalytic formal [3 + 3]-cycloaddition of alpha,beta-unsaturated aldehydes and application to the asymmetric synthesis of (-)-isopulegol hydrate and (-)-cubebaol.

Authors:  Bor-Cherng Hong; Ming-Fun Wu; Hsing-Chang Tseng; Ju-Hsiou Liao
Journal:  Org Lett       Date:  2006-05-25       Impact factor: 6.005

8.  A novel reaction of the "Huisgen zwitterion" with chalcones and dienones: an efficient strategy for the synthesis of pyrazoline and pyrazolopyridazine derivatives.

Authors:  Vijay Nair; Smitha C Mathew; Akkattu T Biju; Eringathodi Suresh
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

9.  Gold-catalyzed [3+3]-annulation of azomethine imines with propargyl esters.

Authors:  Nathan D Shapiro; Yun Shi; F Dean Toste
Journal:  J Am Chem Soc       Date:  2009-08-26       Impact factor: 15.419

10.  Highly enantioselective insertion of carbenoids into N-H bonds catalyzed by copper complexes of chiral spiro bisoxazolines.

Authors:  Bin Liu; Shou-Fei Zhu; Wei Zhang; Chao Chen; Qi-Lin Zhou
Journal:  J Am Chem Soc       Date:  2007-04-12       Impact factor: 15.419
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  12 in total

1.  Highly enantioselective dearomatizing formal [3+3] cycloaddition reactions of N-acyliminopyridinium ylides with electrophilic enol carbene intermediates.

Authors:  Xinfang Xu; Peter Y Zavalij; Michael P Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-02       Impact factor: 15.336

Review 2.  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

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.  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

5.  Dirhodium(II)-catalyzed formal [3+2+1]-annulation of azomethine imines with two molecules of a diazo ketone.

Authors:  Xinfang Xu; Xichen Xu; Peter Y Zavalij; Michael P Doyle
Journal:  Chem Commun (Camb)       Date:  2013-04-07       Impact factor: 6.222

6.  Bicyclic pyrazolidinone derivatives from diastereoselective catalytic [3 + 3]-cycloaddition reactions of enoldiazoacetates with azomethine imines.

Authors:  Yu Qian; Peter J Zavalij; Wenhao Hu; Michael P Doyle
Journal:  Org Lett       Date:  2013-03-11       Impact factor: 6.005

7.  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

8.  Enantioselective cis-β-lactam synthesis by intramolecular C-H functionalization from enoldiazoacetamides and derivative donor-acceptor cyclopropenes.

Authors:  Xinfang Xu; Yongming Deng; David N Yim; Peter Y Zavalij; Michael P Doyle
Journal:  Chem Sci       Date:  2015-04-01       Impact factor: 9.825

9.  The [3 + 3]-cycloaddition alternative for heterocycle syntheses: catalytically generated metalloenolcarbenes as dipolar adducts.

Authors:  Xinfang Xu; Michael P Doyle
Journal:  Acc Chem Res       Date:  2014-03-20       Impact factor: 22.384

10.  Enantioselective synthesis of α-alkenyl α-amino acids via N-H insertion reactions.

Authors:  Jun-Xia Guo; Ting Zhou; Bin Xu; Shou-Fei Zhu; Qi-Lin Zhou
Journal:  Chem Sci       Date:  2015-10-28       Impact factor: 9.825
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