The highly enantioselective aza-Michael
reaction of tert-butyl β-naphthylmethoxycarbamate
to cyclic enones
has been accomplished by using a new cinchona alkaloid
derived C(9)-urea ammonium catalyst under phase-transfer catalysis
conditions with up to 98% ee at 0 °C. The resulting aza-Michael
adducts can be converted to versatile intermediates by selective deprotection
and the cyclic 1,3-aminoalcohols by diastereoselective reduction with
up to 32:1, which have been widely used as important pharmacophores
in pharmaceutical development.
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