Literature DB >> 21162594

Reversal of selectivity in gold-catalyzed cyclizations of 3,3-disubstituted 1,4-diynes.

Roman Rüttinger1, Juliane Leutzow, Michael Wilsdorf, Kristina Wilckens, Constantin Czekelius.   

Abstract

A general synthetic access to 3,3-disubstituted 1,4-diynes bearing a quaternary carbon center from acetylacetone was developed. The compounds were cyclized to the corresponding enol ethers by cationic gold complexes. The reactions occur in complete exo-selectivity in contrast to compounds incorporating an alkoxy substituent in the 3-position. A mechanistic rationale for this reversal of selectivity is provided.

Entities:  

Year:  2010        PMID: 21162594     DOI: 10.1021/ol102628x

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


  3 in total

1.  Triptycene diols: a strategy for synthesizing planar π systems through catalytic conversion of a poly(p-phenylene ethynylene) into a poly(p-phenylene vinylene).

Authors:  Brett VanVeller; Dale Robinson; Timothy M Swager
Journal:  Angew Chem Int Ed Engl       Date:  2011-12-23       Impact factor: 15.336

2.  Facile Access to Cyclooctanoid Ring Systems via Microwave-Assisted Tandem 6-exo dig Cyclization-Rearrangement Sequence.

Authors:  Aaron W Feldman; Sami I Ovaska; Timo V Ovaska
Journal:  Tetrahedron       Date:  2014-07-08       Impact factor: 2.457

3.  Recent advances in the gold-catalyzed additions to C-C multiple bonds.

Authors:  He Huang; Yu Zhou; Hong Liu
Journal:  Beilstein J Org Chem       Date:  2011-07-04       Impact factor: 2.883

  3 in total

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