Literature DB >> 16144376

Pt-catalyzed pentannulations from in situ generated metallo-carbenoids utilizing propargylic esters.

B A Bhanu Prasad1, Francis K Yoshimoto, Richmond Sarpong.   

Abstract

A highly selective and efficient Pt-catalyzed pentannulation reaction beginning from propargylic esters is described. The key to this reaction is the use of a PtCl2(PPh3)2/PhIO catalyst combination that allows the in situ generation of Pt-carbenoid intermediates, which lead to good yields (61-84%) of the desired pentannulated compounds.

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Year:  2005        PMID： 16144376      PMCID： PMC3384518          DOI： 10.1021/ja053192c

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


  11 in total

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

Authors:  Xiaodong Shi; David J Gorin; F Dean Toste
Journal:  J Am Chem Soc       Date:  2005-04-27       Impact factor: 15.419

2.  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

3.  Transition metal salts-catalyzed aza-Michael reactions of enones with carbamates.

Authors:  Shū Kobayashi; Kentaro Kakumoto; Masaharu Sugiura
Journal:  Org Lett       Date:  2002-04-18       Impact factor: 6.005

4.  Catalytic cyclization of o-alkynylbenzaldehyde acetals and thioacetals. Unprecedented activation of the platinum catalyst by olefins. Scope and mechanism of the reaction.

Authors:  Itaru Nakamura; Gan B Bajracharya; Huanyou Wu; Kengo Oishi; Yuya Mizushima; Ilya D Gridnev; Yoshinori Yamamoto
Journal:  J Am Chem Soc       Date:  2004-12-01       Impact factor: 15.419

5.  Rhodium-catalyzed isomerization of alpha-arylpropargyl alcohols to indanones: involvement of an unexpected reaction cascade.

Authors:  Ryo Shintani; Kazuhiro Okamoto; Tamio Hayashi
Journal:  J Am Chem Soc       Date:  2005-03-09       Impact factor: 15.419

6.  Rh(I)-catalyzed cyclization of 1-arylprop-2-yn-1-ol derivatives utilizing rhodium 1,4-migration.

Authors:  Hokuto Yamabe; Akio Mizuno; Hiroyuki Kusama; Nobuharu Iwasawa
Journal:  J Am Chem Soc       Date:  2005-03-16       Impact factor: 15.419

7.  PtCl2-catalyzed cycloisomerizations of 5-en-1-yn-3-ol systems.

Authors:  Youssef Harrak; Christophe Blaszykowski; Matthieu Bernard; Kevin Cariou; Emily Mainetti; Virginie Mouriès; Anne-Lise Dhimane; Louis Fensterbank; Max Malacria
Journal:  J Am Chem Soc       Date:  2004-07-21       Impact factor: 15.419

8.  Platinum- and gold-catalyzed cycloisomerization reactions of hydroxylated enynes.

Authors:  Victor Mamane; Tobias Gress; Helga Krause; Alois Fürstner
Journal:  J Am Chem Soc       Date:  2004-07-21       Impact factor: 15.419

9.  Ruthenium-catalyzed cyclopropanation of alkenes using propargylic carboxylates as precursors of vinylcarbenoids.

Authors:  Koji Miki; Kouichi Ohe; Sakae Uemura
Journal:  J Org Chem       Date:  2003-10-31       Impact factor: 4.354

10.  Pt(IV)-catalyzed cyclization of arene-alkyne substrates via intramolecular electrophilic hydroarylation.

Authors:  Stefan J Pastine; So Won Youn; Dalibor Sames
Journal:  Org Lett       Date:  2003-04-03       Impact factor: 6.005
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  20 in total

1.  Pt-catalyzed cyclization/migration of propargylic alcohols for the synthesis of 3(2H)-furanones, pyrrolones, indolizines, and indolizinones.

Authors:  Eric M Bunnelle; Cameron R Smith; Sharon K Lee; Surendra W Singaram; Allison J Rhodes; Richmond Sarpong
Journal:  Tetrahedron       Date:  2008-02-28       Impact factor: 2.457

2.  The use of Br/Cl to promote regioselective gold-catalyzed rearrangement of propargylic carboxylates: an efficient synthesis of (1Z, 3E)-1-bromo/chloro-2-carboxy-1,3-dienes.

Authors:  Yanzhao Wang; Biao Lu; Liming Zhang
Journal:  Chem Commun (Camb)       Date:  2010-10-29       Impact factor: 6.222

3.  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

4.  Gold-catalyzed intramolecular allylation of silyl alkynes induced by silane alcoholysis.

Authors:  Sangho Park; Daesung Lee
Journal:  J Am Chem Soc       Date:  2006-08-23       Impact factor: 15.419

5.  Remarkable facilitation of hetero-cycloisomerizations with water and other polar protic solvents: metal-free synthesis of indolizines.

Authors:  Alison R Hardin Narayan; Richmond Sarpong
Journal:  Green Chem       Date:  2010       Impact factor: 10.182

6.  Interception of a Rautenstrauch intermediate by alkynes for [5+2] cycloaddition: rhodium-catalyzed cycloisomerization of 3-acyloxy-4-ene-1,9-diynes to bicyclo[5.3.0]decatrienes.

Authors:  Xing-zhong Shu; Suyu Huang; Dongxu Shu; Ilia A Guzei; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-11       Impact factor: 15.336

Review 7.  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

8.  Substituent Effect on the Formation and Their Reactivity of Platinum Carbenoids.

Authors:  Eun Jin Cho; Daesung Lee
Journal:  Adv Synth Catal       Date:  2008-11-17       Impact factor: 5.837

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.  Mechanistically diverse copper-, silver-, and gold-catalyzed acyloxy and phosphatyloxy migrations: efficient synthesis of heterocycles via cascade migration/cycloisomerization approach.

Authors:  Todd Schwier; Anna W Sromek; Dahrika M L Yap; Dmitri Chernyak; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2007-07-21       Impact factor: 15.419
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