1.
J Org Chem
; 78(16): 7970-6, 2013 Aug 16.
Article
in English
| MEDLINE
| ID: mdl-23875583
ABSTRACT
A distinct chemoselectivity in the gold-catalyzed oxidative cyclization of 3,5-dien-1-ynes was observed when 3,5-dichloropyridine N-oxide replaced 8-methylquinoline N-oxide as the oxidant; the resulting cyclopentadienyl aldehydes were obtained in good yields. The altered chemoselectivity is attributed to a prior enyne cyclization in the presence of 3,5-dichloropyridine N-oxides. The use of N-iminopyridium ylide enables a similar iminocyclization reaction to give cyclopentadienyl imines efficiently. Our experimental data support a prior gold-catalyzed cyclization of 3,5-dien-1-ynes to form gold carbene, followed by the oxidation with N-oxide.
Subject(s)
Aldehydes/chemical synthesis , Alkynes/chemistry , Organogold Compounds/chemistry , Aldehydes/chemistry , Catalysis , Cyclization , Molecular Structure , Oxidation-Reduction
2.
Angew Chem Int Ed Engl
; 50(30): 6911-4, 2011 Jul 18.
Article
in English
| MEDLINE
| ID: mdl-21648044
3.
Angew Chem Int Ed Engl
; 49(51): 9891-4, 2010 Dec 17.
Article
in English
| MEDLINE
| ID: mdl-21089084