Literature DB >> 26273112

Gold(I)-catalyzed enantioselective [3+2] and [3+3] cycloaddition reactions of propargyl acetals/ketals.

Cristina Navarro1, Nathan D Shapiro1, Maurizio Bernasconi1, Takahiro Horibe1, F Dean Toste1.   

Abstract

An asymmetric gold(I)-catalyzed [3+2] cycloaddition of propargyl acetals/ketals and aldehydes is reported, which proceeds via stepwise migration-fragmentation of acetals/ketals and cycloaddition of the in situ generated gold-carbenoid intermediate. Various functionalized 2, 5-dihydrofurans were obtained in good yields and high enantioselectivities. Furthermore, an example of the first gold(I) catalyzed [3+3] cycloaddition of secondary propargyl ketals and nitrones is presented.

Entities:  

Keywords:  Cycloaddition; Enantioselective catalysis; Gold; Homogeneous catalysis; Propargyl acetals/ketals

Year:  2015        PMID： 26273112      PMCID： PMC4528387          DOI： 10.1016/j.tet.2015.04.109

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  38 in total

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Journal:  J Am Chem Soc       Date:  2009-09-16       Impact factor: 15.419

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

Authors:  Koji Miki; Kouichi Ohe; Sakae Uemura
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8.  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

9.  Rhodium(II)- and copper(II)-catalyzed reactions of enol diazoacetates with nitrones: metal carbene versus Lewis acid directed pathways.

Authors:  Yu Qian; Xinfang Xu; Xiaochen Wang; Peter J Zavalij; Wenhao Hu; Michael P Doyle
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10.  Fluorenes and styrenes by Au(I)-catalyzed annulation of enynes and alkynes.

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  1 in total

Review 1.  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
  1 in total

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