Download PDF
Synfacts 2023; 19(11): 1123
DOI: 10.1055/s-0042-1752261
Metals in Synthesis

Development of Chiral Gold and Platinum Complexes for Enantioselective Alkoxycyclization of Enynes

Contributor(s):
Mark Lautens
,
Aurélien Dupeux
Munõz MP, Adrio J, Carretero JC, Echavarren AM. * Universidad Autónoma de Madrid and Institute of Chemical Research of Catalonia (ICIQ), Tarragona, Spain
Ligand Effects in Gold- and Platinum-Catalyzed Cyclization of Enynes: Chiral Gold Complexes for Enantioselective Alkoxycyclization.

Organometallics 2005;
24: 1293-1300
DOI: 10.1021/om0491645
CrossrefSearch in Google Scholar
› Further Information
 
 PDF Download Permissions and Reprints

Key words

gold catalysis - platinum catalysis - alkoxycyclization - enantioselectivity - tandem reaction

Significance

The group of Echavarren developed an enantioselective gold- and platinum-catalyzed alkoxycyclization of 1,6-enynes. A ligand study shows that the Alder-ene-type cyclization could be inhibited by using phosphine and bidentate N-N ­ligands. Under these conditions, the tandem cycloisomerization/alkoxylation reaction is favored. Enantioselectivity is generally modest, but has paved the way for additional studies.


#

Comment

Gold- and platinum-catalyzed cyclo­isomerization of 1,6-enynes are well known. Enantio­selective reactions using gold(I) complexes are sometimes challenging due to the linear geometry of the complexes. Here, the authors presented the first gold-catalyzed alkoxycyclization reaction. Numerous chiral gold(I) complexes have been synthesized, isolated and crystallized for X-ray analysis.


#
#

Publication History

Article published online:
14 October 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany


   Permissions and Reprints