Scandium-catalyzed carbon-carbon bond formations using alpha-organosulfanyl and organoselanyl-alpha-fluoroacetic acid derivatives.
The scandium-catalyzed reactions of alpha-organosulfanyl and organoselanyl-alpha-fluoroacetates 1-2, acetamides 3-4 and acetonitrile 5 with soft nucleophiles proceeded to give the products 6a-b, 7a-c, 8a-c, 9a-e in good to high yields. We also successfully performed the scandium-catalyzed intramolecular cyclization reactions and obtained the unique 5-methylene-2-oxotetrahydropyrans 16-17.
Gotoh
Kohei
K
Department of Chemistry, Faculty of Education, Gifu University, Gifu, Japan.
Yamamoto
Teruhisa
T
Yoshimatsu
Mitsuhiro
M
D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D005463:Fluoroacetates / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012538:Scandium / Q000737:chemistry*; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000737:chemistry*
D005463:Fluoroacetates; D013457:Sulfur Compounds; D002244:Carbon; C014815:fluoroacetic acid; D012538:Scandium