- Ruthenium Tetroxide Oxidation of 1-Azabicycloalkan-2-ones
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The ruthenium tetroxide (RuO4) oxidation of 1-azabicycloalkan-2-ones was investigated.The oxidation of quinolizidin-4-one (4), indolizidin-3-one (9), pyrrolizidin-3-one (11) and tetrahydro-1H,3H-pyrrolooxazol-3-one (12) occured at the bridgehead tertiary carbon atom and afforded the corresponding hydroxy compounds (from 11 and 12) or the imidobutyric acid derivatives (from 4 and 9).This regioselectivity is contrary to the general situation in the oxidation of N-acyl cyclic amines.Howewer, 1-azabicyclooctan-8-one (17) was oxidized at the secondary carbon atom to give the 2,8-dione (18).Keywords: oxidation; ruthenium tetroxide oxidation; hydroxylation; regioselectivity; 1-azabicycloalkan-2-one; ruthenium tetroxide; two-phase method
- Yoshifuji, Shigeyuki,Arakawa, Yukimi,Nitta, Yoshihiro
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p. 5042 - 5047
(2007/10/02)
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