Literature DB >> 17629294

Gold(I)-catalyzed cascade cyclization reaction: highly regio- and diastereoselective intermolecular addition of water and alcohols to epoxy alkynes.

Lun-Zhi Dai1, Ming-Juan Qi, Yong-Ling Shi, Xu-Guang Liu, Min Shi.   

Abstract

We have developed a novel access to ketal skeletons through a highly regio- and diastereoselective intermolecular addition of water and alcohols to alkynyl epoxides catalyzed by gold(I). This procedure involves a domino three-membered ring-opening, 6-exo-cycloisomerization, and subsequent intra- or intermolecular nucleophilic addition to a double-bond sequence.

Entities:  

Year:  2007        PMID: 17629294     DOI: 10.1021/ol0713640

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  6 in total

1.  Formal [4+3] epoxide cascade reaction via a complementary ambiphilic pairing strategy.

Authors:  Alan Rolfe; Thiwanka B Samarakoon; Paul R Hanson
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

2.  Gold(I)-catalyzed cascade cyclization of allenyl epoxides.

Authors:  Michael A Tarselli; J Lucas Zuccarello; Stephen J Lee; Michel R Gagné
Journal:  Org Lett       Date:  2009-08-06       Impact factor: 6.005

Review 3.  Ligand effects in homogeneous Au catalysis.

Authors:  David J Gorin; Benjamin D Sherry; F Dean Toste
Journal:  Chem Rev       Date:  2008-07-25       Impact factor: 60.622

4.  Synthetic applications of gold-catalyzed ring expansions.

Authors:  David Garayalde; Cristina Nevado
Journal:  Beilstein J Org Chem       Date:  2011-06-07       Impact factor: 2.883

5.  Gold-catalyzed reaction of oxabicyclic alkenes with electron-deficient terminal alkynes to produce acrylate derivatives.

Authors:  Yin-Wei Sun; Qin Xu; Min Shi
Journal:  Beilstein J Org Chem       Date:  2013-10-01       Impact factor: 2.883

6.  Silver(I)-Catalyzed Intramolecular Cyclizations of Epoxide-Propargylic Esters to 1,4-Oxazine Derivatives.

Authors:  Peng-Hua Li; Jin-Ming Yang; Yin Wei; Min Shi
Journal:  ChemistryOpen       Date:  2016-12-13       Impact factor: 2.911

  6 in total

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