Literature DB >> 15079081

Palladium-catalyzed carbocyclization of 1,6-enynes leading to six-membered rings or oxidized five-membered trifluoroacetates.

Koichi Mikami1, Manabu Hatano.   

Abstract

We describe palladium-catalyzed carbocyclization of 1,6-enynes leading to six-membered rings by water-originated hydride addition. Mechanistic features of this anomalous carbocyclization and isolation of a chiral five-membered C-Pd intermediate as an oxidized form of trifluoroacetate are also reported.

Entities:  

Year:  2004        PMID： 15079081      PMCID： PMC395982          DOI： 10.1073/pnas.0307217101

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN： 0027-8424            Impact factor:   11.205


  11 in total

1.  The development of L2X2Ru=CHR olefin metathesis catalysts: an organometallic success story.

Authors:  T M Trnka; R H Grubbs
Journal:  Acc Chem Res       Date:  2001-01       Impact factor: 22.384

2.  Transition Metal-Catalyzed Carbocyclizations in Organic Synthesis.

Authors:  Iwao Ojima; Maria Tzamarioudaki; Zhaoyang Li; Robert J. Donovan
Journal:  Chem Rev       Date:  1996-03-28       Impact factor: 60.622

3.  The behavior of 1,n-enynes in the presence of transition metals.

Authors:  Corinne Aubert; Olivier Buisine; Max Malacria
Journal:  Chem Rev       Date:  2002-03       Impact factor: 60.622

4.  A boronic ester annulation strategy for diversity-oriented organic synthesis.

Authors:  Glenn C Micalizio; Stuart L Schreiber
Journal:  Angew Chem Int Ed Engl       Date:  2002-01-04       Impact factor: 15.336

5.  Highly Enantioselective Palladium-Catalyzed Ene-Type Cyclization of a 1,6-Enyne We are grateful to Drs. H. Kumobayashi, T. Miura, and N. Sayo of Takasago International Co. for providing the BINAP and SEGPHOS ligands. We also thank Dr. M. Yamasaki and Mr. S. Sato of RIGAKU Co. for the X-ray analyses.

Authors:  Manabu Hatano; Masahiro Terada; Koichi Mikami
Journal:  Angew Chem Int Ed Engl       Date:  2001-01-05       Impact factor: 15.336

6.  Platinum-catalyzed cycloisomerization reactions of enynes.

Authors:  A Fürstner; F Stelzer; H Szillat
Journal:  J Am Chem Soc       Date:  2001-12-05       Impact factor: 15.419

7.  Ru(II)- and Pt(II)-catalyzed cycloisomerization of omega-aryl-1-alkynes. Generation Of carbocationic species from alkynes and transition metal halides and its interception by an aromatic ring

Authors: 
Journal:  J Org Chem       Date:  2000-08-11       Impact factor: 4.354

8.  Chiral Palladium(II)-catalyzed asymmetric glyoxylate-Ene reaction: alternative approach to the enantioselective synthesis of alpha-hydroxy esters

Authors: 
Journal:  Org Lett       Date:  2000-12-14       Impact factor: 6.005

9.  Cyclizations of enynes catalyzed by PtCl2 or other transition metal chlorides: divergent reaction pathways.

Authors:  M Méndez; M P Muñoz; C Nevado; D J Cárdenas; A M Echavarren
Journal:  J Am Chem Soc       Date:  2001-10-31       Impact factor: 15.419

10.  Highly enantioselective quinoline synthesis via ene-type cyclization of 1,7-enynes catalyzed by a cationic BINAP-palladium(II) complex.

Authors:  Manabu Hatano; Koichi Mikami
Journal:  J Am Chem Soc       Date:  2003-04-23       Impact factor: 15.419
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  1 in total

1.  Asymmetric Au-catalyzed cycloisomerization of 1,6-enynes: An entry to bicyclo[4.1.0]heptene.

Authors:  Alexandre Pradal; Chung-Meng Chao; Patrick Y Toullec; Véronique Michelet
Journal:  Beilstein J Org Chem       Date:  2011-07-26       Impact factor: 2.883
  1 in total

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