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Use of Planar Chiral Ferrocenylphosphine‐Gold(I) Complexes in the Asymmetric Cycloisomerization of 3‐Hydroxylated 1,5‐Enynes
Author(s) -
Wu Zhiyong,
Retailleau Pascal,
Gandon Vincent,
Voituriez Arnaud,
Marinetti Angela
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501121
Subject(s) - cycloisomerization , chemistry , phosphine , enantioselective synthesis , denticity , catalysis , ferrocene , stereochemistry , combinatorial chemistry , bicyclic molecule , medicinal chemistry , organic chemistry , crystal structure , electrode , electrochemistry
Chiral monodentate phosphines based on ortho ‐disubstituted ferrocene units have been prepared and used for the synthesis of gold(I) complexes. These complexes are highly active catalysts for the cycloisomerization of 3‐hydroxy‐1,5‐enynes into bicyclo[3.1.0]hexanones. Their high catalytic activity is ascribed to their structural analogy to the biaryl‐based Buchwald phosphines. This paper discloses the first enantioselective variant of these reactions based on gold catalysis ( ee 's up to 80 %).