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Highly Diastereoselective Catalytic Meerwein−Ponndorf−Verley Reductions
journal contribution
posted on 2006-01-20, 00:00 authored by Jingjun Yin, Mark A. Huffman, Karen M. Conrad, Joseph D. ArmstrongVery practical synthesis of ephedrine analogues in high yields
and enantiopurity was realized by a highly diastereoselective
Meerwein−Ponndorf−Verley (MPV) reduction of protected
α-amino aromatic ketones using catalytic aluminum isopropoxide. The high anti selectivity resulted from the chelation
of the nitrogen anion to the aluminum. In contrast, high syn
selectivity was obtained with α-alkoxy ketones and other
compounds via Felkin−Ahn control.