Literature DB >> 15839674

Synthesis of 2-cyclopentenones by gold(I)-catalyzed Rautenstrauch rearrangement.

Xiaodong Shi1, David J Gorin, F Dean Toste.   

Abstract

The rearrangement of 1-ethynyl-2-propenyl pivaloates to cyclopentenones catalyzed by cationic triphenylphosphinegold(I) complexes is described. The reaction tolerates both alkyl and aryl substitution at the acetylenic and olefinic positions. Importantly, the gold(I)-catalyzed rearrangement of enantioenriched propargyl pivaloates proceeds with excellent chirality transfer, thus providing a practical method for the enantioselective synthesis of cyclopentenones.

Entities:  

Year:  2005        PMID： 15839674     DOI： 10.1021/ja051689g

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


  39 in total

1.  Dinuclear Zn-catalyzed asymmetric alkynylation of unsaturated aldehydes.

Authors:  Barry M Trost; Andrew H Weiss; Axel Jacobi von Wangelin
Journal:  J Am Chem Soc       Date:  2006-01-11       Impact factor: 15.419

2.  A divergent mechanistic course of Pd(0)-catalyzed aza-Claisen rearrangement and aza-Rautenstrauch-type cyclization of N-allyl ynamides.

Authors:  Kyle A Dekorver; Richard P Hsung; Andrew G Lohse; Yu Zhang
Journal:  Org Lett       Date:  2010-04-16       Impact factor: 6.005

3.  Gold-catalyzed 1,2-migration of silicon, tin, and germanium en route to C-2 substituted fused pyrrole-containing heterocycles.

Authors:  Ilya V Seregin; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2006-09-20       Impact factor: 15.419

4.  Rhodium-catalyzed intra- and intermolecular [5 + 2] cycloaddition of 3-acyloxy-1,4-enyne and alkyne with concomitant 1,2-acyloxy migration.

Authors:  Xing-Zhong Shu; Xiaoxun Li; Dongxu Shu; Suyu Huang; Casi M Schienebeck; Xin Zhou; Patrick J Robichaux; Weiping Tang
Journal:  J Am Chem Soc       Date:  2012-03-12       Impact factor: 15.419

5.  Recent Advances in Transition Metal-Catalyzed Glycosylation.

Authors:  Matthew J McKay; Hien M Nguyen
Journal:  ACS Catal       Date:  2012-06-14       Impact factor: 13.084

6.  Multisubstituted N-fused heterocycles via transition metal-catalyzed cycloisomerization protocols.

Authors:  Ilya V Seregin; Alex W Schammel; Vladimir Gevorgyan
Journal:  Tetrahedron       Date:  2008-07-14       Impact factor: 2.457

7.  4-Butyl-3-(3,5-dimethoxy-phen-yl)-4-meth-oxy-2-(triisopropyl-silyl)cyclopent-2-enone.

Authors:  Zhenyu Zhao; Yunhui Zhang; Xinghua Jin; Xinjian Yang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-01-25

8.  Synthesis of cyclopentenimines from N-allyl ynamides via a tandem aza-Claisen rearrangement-carbocyclization sequence.

Authors:  Xiao-Na Wang; Gabrielle N Winston-McPherson; Mary C Walton; Yu Zhang; Richard P Hsung; Kyle A DeKorver
Journal:  J Org Chem       Date:  2013-06-10       Impact factor: 4.354

Review 9.  Metal-catalyzed double migratory cascade reactions of propargylic esters and phosphates.

Authors:  Roohollah Kazem Shiroodi; Vladimir Gevorgyan
Journal:  Chem Soc Rev       Date:  2013-06-21       Impact factor: 54.564

10.  Enantioselective synthesis of 5,7-bicyclic ring systems from axially chiral allenes using a Rh(I)-catalyzed cyclocarbonylation reaction.

Authors:  Francois Grillet; Kay M Brummond
Journal:  J Org Chem       Date:  2013-03-29       Impact factor: 4.354
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