-transparent.png){kind=logo}
Palladium-catalyzed cyclization reactions of 2-vinylthiiranes with heterocumulenes. Regioselective and enantioselective formation of thiazolidine, oxathiolane, and dithiolane derivatives. 2001
Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, Canada K1N 6N5.
The first palladium-catalyzed ring-expansion reaction of 2-vinylthiiranes with heterocumulenes to form sulfur-containing five-membered-ring heterocycles is described. This regioselective reaction requires 5 mol % of Pd(2)(dba)(3).CHCl(3) and 10 mol % of bidendate phosphine ligand (dppp, BINAP), at 50-80 degrees C, in THF. The reaction of 2-vinylthiiranes with carbodiimides, isocyanates, and ketenimines affords 1,3-thiazolidine derivatives, whereas the reaction with diphenylketene or isothiocyanates results in the formation of 1,3-oxathiolane or 1,3-dithiolane compounds in good to excellent isolated yields and in up to 78% ee.
Related Publications
C Larksarp, and
O Sellier, and
H Alper
May 2000,
The Journal of organic chemistry,
C Larksarp, and
O Sellier, and
H Alper
June 2015,
The Journal of organic chemistry,
C Larksarp, and
O Sellier, and
H Alper
April 2018,
Organic letters,
C Larksarp, and
O Sellier, and
H Alper
May 2015,
Angewandte Chemie (International ed. in English),
C Larksarp, and
O Sellier, and
H Alper
April 2014,
Chemical communications (Cambridge, England),
C Larksarp, and
O Sellier, and
H Alper
January 2016,
Organic letters,
C Larksarp, and
O Sellier, and
H Alper
December 2006,
Organic letters,
C Larksarp, and
O Sellier, and
H Alper
March 2007,
Journal of the American Chemical Society,
C Larksarp, and
O Sellier, and
H Alper
December 2019,
Chemistry, an Asian journal,
C Larksarp, and
O Sellier, and
H Alper
March 1975,
Die Pharmazie,
