Helvetica Chimica Acta p. 554 - 569 (1987)
Update date:2022-08-05
Topics:
Defoin, Albert
Fritz, Hans
Schmidlin, Christian
Streith, Jacques
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 <2> 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.
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