Michael reactions on conformationally flexible methyl 3-C-nitro-hex-2-enopyranoside derivatives.
Dimethyl malonate and dibenzoylmethane attacked the C-2 position of the title 3-nitro-2-enopyranosides from the side opposite the anomeric methoxyl group to afford the 3-enopyranosides (S(N)2' products). In the case of 2,4-pentanedione and ethyl acetoacetate, further intramolecular cyclization occurred to yield dihydropyran derivatives.
Sakakibara
T
T
Faculty of Science, Yokohama City University, Seto, Yokohama, Japan.
Tokuda
K
K
Hayakawa
T
T
Seta
A
A
D002236:Carbohydrate Conformation; D006027:Glycosides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009574:Nitro Compounds / Q000737:chemistry*; D018583:Pliability
D006027:Glycosides; D009574:Nitro Compounds