Literature DB >> 18217767

Au-catalyzed cyclization of monoallylic diols.

Aaron Aponick1, Chuan-Ying Li, Berenger Biannic.   

Abstract

The Ph3PAuCl/AgOTf-catalyzed cyclization of monoallylic diols to form tetrahydropyrans is reported. The reactions proceed rapidly at temperatures as low as -78 degrees C with catalyst loadings as low as 0.1 mol % to provide the products in 79-99% yield. A broad range of structurally diverse substrates perform well in the reaction. When 2,6-disubstituted tetrahydropyrans are produced, the reaction is highly diastereoselective for the 2,6-cis product.

Entities:  

Year:  2008        PMID： 18217767     DOI： 10.1021/ol703002p

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


  11 in total

1.  Gold(I)-catalyzed amination of allylic alcohols with cyclic ureas and related nucleophiles.

Authors:  Paramita Mukherjee; Ross A Widenhoefer
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

2.  Gold(I)-catalyzed intramolecular amination of allylic alcohols with alkylamines.

Authors:  Paramita Mukherjee; Ross A Widenhoefer
Journal:  Org Lett       Date:  2011-02-11       Impact factor: 6.005

3.  Re2 O7 -Mediated Dehydrative Cyclization Reactions: Total Synthesis of Herboxidiene and Its 12-Desmethyl Analogue.

Authors:  Tyler M Rohrs; Qi Qin; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-28       Impact factor: 15.336

4.  The regio- and stereospecific intermolecular dehydrative alkoxylation of allylic alcohols catalyzed by a gold(I) N-heterocyclic carbene complex.

Authors:  Paramita Mukherjee; Ross A Widenhoefer
Journal:  Chemistry       Date:  2013-01-24       Impact factor: 5.236

5.  Efficient gold(I)/silver(I)-cocatalyzed cascade intermolecular N-Michael addition/intramolecular hydroalkylation of unactivated alkenes with α-ketones.

Authors:  Ya-Ping Xiao; Xin-Yuan Liu; Chi-Ming Che
Journal:  Beilstein J Org Chem       Date:  2011-08-11       Impact factor: 2.883

6.  A comparative study of the Au-catalyzed cyclization of hydroxy-substituted allylic alcohols and ethers.

Authors:  Berenger Biannic; Thomas Ghebreghiorgis; Aaron Aponick
Journal:  Beilstein J Org Chem       Date:  2011-06-14       Impact factor: 2.883

7.  Gold(I)-catalyzed synthesis of γ-vinylbutyrolactones by intramolecular oxaallylic alkylation with alcohols.

Authors:  Michel Chiarucci; Mirko Locritani; Gianpiero Cera; Marco Bandini
Journal:  Beilstein J Org Chem       Date:  2011-09-01       Impact factor: 2.883

8.  Gold(I)-catalysed one-pot synthesis of chromans using allylic alcohols and phenols.

Authors:  Eloi Coutant; Paul C Young; Graeme Barker; Ai-Lan Lee
Journal:  Beilstein J Org Chem       Date:  2013-09-04       Impact factor: 2.883

9.  Chirality Transfer in Gold(I)-Catalysed Direct Allylic Etherifications of Unactivated Alcohols: Experimental and Computational Study.

Authors:  Graeme Barker; David G Johnson; Paul C Young; Stuart A Macgregor; Ai-Lan Lee
Journal:  Chemistry       Date:  2015-08-06       Impact factor: 5.236

10.  Gold(I)-catalysed direct thioetherifications using allylic alcohols: an experimental and computational study.

Authors:  Lorena Herkert; Samantha L J Green; Graeme Barker; David G Johnson; Paul C Young; Stuart A Macgregor; Ai-Lan Lee
Journal:  Chemistry       Date:  2014-07-30       Impact factor: 5.236
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