First asymmetric hetero Diels-Alder reaction of 1-sulfinyl dienes with nitroso derivatives. A new entry to the synthesis of optically pure 1,4-imino-L-ribitol derivatives.
Hetero Diels-Alder (HDA) cycloaddition of chiral 1-p-tolylsulfinyl-1,3-pentadiene with benzyl nitrosoformate, under mild conditions, yields 2H-1,2-oxazine 3 with complete regioselectivity and pi-facial diastereoselectivity. Sequential osmylation and protection of the resulting glycol gives the oxazine 5 which is directly transformed into enantiomerically pure 1,4,5-trideoxy-1,4-imino-L-ribitol 8 by reduction under Pd/C.
Arribas
C
C
Departamento de Química Orgánica (E.T.S.I.I.), Universidad de Valladolid, Paseo del Cauce s/n, 47011, Valladolid, Spain.
Carreño
M C
MC
García-Ruano
J L
JL
Rodríguez
J F
JF
Santos
M
M
Sanz-Tejedor
M A
MA
D003500:Cyclization; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D009603:Nitroso Compounds / Q000737:chemistry*; D012255:Ribitol / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D013237:Stereoisomerism
D004791:Enzyme Inhibitors; D007202:Indicators and Reagents; D009603:Nitroso Compounds; D012255:Ribitol; D006026:Glycoside Hydrolases