94936-55-7Relevant articles and documents
Syntheses of Diamino-dideoxylyxose Derivatives using Acylnitroso Dienophiles
Defoin, Albert,Fritz, Hans,Schmidlin, Christian,Streith, Jacques
, p. 554 - 569 (2007/10/02)
N-Acylnitroso derivatives 6 which were prepared by in-situ oxidation of the corresponding hydroxamic acids 5 reacted instantaneously and in high yields with dihydropyridine 4.The Diels-Alder adducts 8 were formed regiospecifically with the acylnitroso dienophiles 6a-c, whereas the dienophiles 6d-f gave mixtures of both regioisomers 7 and 8.These and some other results were best explained by the FMO theory.The Diels-Alder adducts 7 and 8 gave the corresponding 'anti'-cis-glycols when reacted with OsO4/N-methylmorpholine N-oxide.Hydrogenolysis of the N-O bond folloved by peracetylation led to the expected aminolyxose derivatives 14 and 16.A similar sequence, using 4 and the hydroxamic-acid derivative 18 of (+)-D-mandelic acid led, with a poor assymmetric induction, to a mixture of the expected optically active aminolyxose compounds 19A/19B.
SYNTHESIS OF RACEMIC DIAMINO-DIDEOXY-LYXOPYRANOSE DERIVATIVES USING ACILNITROSO DIENOPHILES (1).
Defoin, Albert,Schmidlin, Christian,Streith, Jacques
, p. 4515 - 4518 (2007/10/02)
Acylnitroso derivatives, which are obtained by in situ oxidation of the corresponding hydroxamic acids with tetraalkylammonium iodate, react intantaneously in the presence of dihydropyridine 1 leading to the Diels-Alder adducts 4 and 5.These latter ones w
