Bicyclo[3.3.1]nonanes as synthetic intermediates. Part 19. Asymmetric cleavage of ω-azabicyclo[3.n.1]alkan-3-ones at the 'fork head'
Asymmetric cleavage of ω-azabicyclo[3.n.1]alkan-3-ones was achieved by asymmetric deprotonation at the 'fork head' ketone system with Koga's chiral base and subsequent ozonolysis of the resulting chiral silyl enol ether to give the cis-α,α′-disubstituted piperidine, pyrrolidine and hexahydroazepine, respectively, in high enantiomeric excess.
Momose, Takefumi,Toshima, Minoru,Toyooka, Naoki,Hirai, Yoshiro,Eugster, Conrad Hans
p. 1307 - 1313
(2007/10/03)
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