Literature DB >> 22252254

Rhodium-catalyzed 1,3-acyloxy migration and subsequent intramolecular [4+2] cycloaddition of vinylallene and unactivated alkyne.

Suyu Huang1, Xiaoxun Li, Claire L Lin, Ilia A Guzei, Weiping Tang.   

Abstract

A Rh-catalyzed 1,3-acyloxy migration of propargyl ester followed by intramolecular [4+2] cycloaddition of vinylallene and unactivated alkyne was developed. This tandem reaction provides access to bicyclic compounds containing a highly functionalized isotoluene or cyclohexenone structural motif, while only aromatic compounds were observed in related transition metal-catalyzed cycloadditions. This journal is © The Royal Society of Chemistry 2012

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Year:  2012        PMID： 22252254      PMCID： PMC3334501          DOI： 10.1039/c2cc17406e

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  16 in total

1.  Transition Metal-Mediated Cycloaddition Reactions.

Authors:  Mark Lautens; Wolfgang Klute; William Tam
Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

2.  Tandem Dielsminus signAlder Cycloadditions in Organic Synthesis.

Authors:  Jeffrey D. Winkler
Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

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Authors:  Hans-Werner Frühauf
Journal:  Chem Rev       Date:  1997-05-08       Impact factor: 60.622

4.  Formal [2 + 2 + 2] cycloaddition strategy based on an intramolecular propargylic ene reaction/Diels-Alder cycloaddition cascade.

Authors:  Julia M Robinson; Takeo Sakai; Katsuhiko Okano; Takafumi Kitawaki; Rick L Danheiser
Journal:  J Am Chem Soc       Date:  2010-08-18       Impact factor: 15.419

Review 5.  Recent advances in natural product synthesis by using intramolecular Diels-Alder reactions.

Authors:  Ken-Ichi Takao; Ryosuke Munakata; Kin-ichi Tadano
Journal:  Chem Rev       Date:  2005-12       Impact factor: 60.622

Review 6.  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

7.  Rhodium-catalyzed ring expansion of cyclopropanes to seven-membered rings by 1,5 C-C bond migration.

Authors:  Xiaoxun Li; Min Zhang; Dongxu Shu; Patrick J Robichaux; Suyu Huang; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-09       Impact factor: 15.336

8.  Synthesis of highly functionalized cyclohexenone rings: rhodium-catalyzed 1,3-acyloxy migration and subsequent [5+1] cycloaddition.

Authors:  Dongxu Shu; Xiaoxun Li; Min Zhang; Patrick J Robichaux; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-29       Impact factor: 15.336

9.  Transition metal catalyzed cycloisomerizations of 1,n-allenynes and -allenenes.

Authors:  Corinne Aubert; Louis Fensterbank; Pierre Garcia; Max Malacria; Antoine Simonneau
Journal:  Chem Rev       Date:  2011-03-09       Impact factor: 60.622

10.  Cycloisomerization of 1,n-enynes: challenging metal-catalyzed rearrangements and mechanistic insights.

Authors:  Véronique Michelet; Patrick Y Toullec; Jean-Pierre Genêt
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336
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  6 in total

1.  Rhodium-catalyzed carbonylation of 3-acyloxy-1,4-enynes for the synthesis of cyclopentenones.

Authors:  Xiaoxun Li; Suyu Huang; Casi M Schienebeck; Dongxu Shu; Weiping Tang
Journal:  Org Lett       Date:  2012-03-02       Impact factor: 6.005

Review 2.  Rhodium-catalyzed acyloxy migration of propargylic esters in cycloadditions, inspiration from the recent "gold rush".

Authors:  Xing-Zhong Shu; Dongxu Shu; Casi M Schienebeck; Weiping Tang
Journal:  Chem Soc Rev       Date:  2012-12-07       Impact factor: 54.564

3.  Generation of rhodium(I) carbenes from ynamides and their reactions with alkynes and alkenes.

Authors:  Renhe Liu; Gabrielle N Winston-McPherson; Zhong-Yue Yang; Xin Zhou; Wangze Song; Ilia A Guzei; Xiufang Xu; Weiping Tang
Journal:  J Am Chem Soc       Date:  2013-05-23       Impact factor: 15.419

4.  Rhodium- and platinum-catalyzed [4+3] cycloaddition with concomitant indole annulation: synthesis of cyclohepta[b]indoles.

Authors:  Dongxu Shu; Wangze Song; Xiaoxun Li; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2013-02-10       Impact factor: 15.336

5.  Rhodium-Catalyzed Stereoselective Intramolecular [5 + 2] Cycloaddition of 3-Acyloxy 1,4-Enyne and Alkene.

Authors:  Xing-zhong Shu; Casi M Schienebeck; Xiaoxun Li; Xin Zhou; Wangze Song; Lianqing Chen; Ilia A Guzei; Weiping Tang
Journal:  Org Lett       Date:  2015-10-06       Impact factor: 6.005

6.  Rhodium-catalyzed carbonylation of cyclopropyl substituted propargyl esters: a tandem 1,3-acyloxy migration [5 + 1] cycloaddition.

Authors:  Dongxu Shu; Xiaoxun Li; Min Zhang; Patrick J Robichaux; Ilia A Guzei; Weiping Tang
Journal:  J Org Chem       Date:  2012-07-25       Impact factor: 4.354
  6 in total

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