Lewis base catalyzed 1,3-dithiane addition to carbonyl and imino compounds using 2-trimethylsilyl-1,3-dithiane.
Lewis base-catalyzed 1,3-dithiane addition to electrophiles such as carbonyl compounds and N-substituted aldimines with 2-trimethylsilyl-1,3-dithiane (TMS-dithiane) is described. By the activation of the carbon-silicon bond in the presence of a Lewis base catalyst such as tetrabutylammonium phenoxide (PhONnBu(4)), a 1,3-dithiane addition reaction proceeded smoothly to afford the corresponding adducts in good to high yields under mild conditions. This synthesis is also applied to the reactions of ketones having alpha-protons, and of N-substituted aldimines.
The Kitasato Institute, Center for Basic Research, 6-15-5 (TCI) Toshima, Kita-ku, Tokyo 114-0003, Japan.
Makoto
M
Michida
Teruaki
T
Mukaiyama
D000447:Aldehydes / Q000737:chemistry; D000468:Alkalies / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D004583:Electrons; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D007097:Imines / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry; D012997:Solvents
D000447:Aldehydes; D000468:Alkalies; D002264:Carboxylic Acids; D006571:Heterocyclic Compounds; D007097:Imines; D012997:Solvents; C012947:1,3-dithiane; D009584:Nitrogen