Double bond isomerization/enantioselective aza-Petasis-Ferrier rearrangement sequence as an efficient entry to anti- and enantioenriched beta-amino aldehydes.
Highly anti- and enantioselective synthesis of beta-amino aldehydes having an aliphatic substituent at the beta-position was accomplished by a combination of two catalytic reactions, that is, an initial Ni(II) complex-catalyzed isomerization of a double bond followed by a chiral phosphoric acid catalyzed aza-Petasis-Ferrier rearrangement, using hemiaminal allyl ethers as the initial substrate. The chiral phosphoric acid also functioned as an efficient resolving catalyst of racemic hemiaminal vinyl ethers.
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan.
Masahiro
M
Terada
Yasunori
Y
Toda
D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D004987:Ethers; D013237:Stereoisomerism; D014753:Vinyl Compounds
D000447:Aldehydes; D000475:Alkenes; D004987:Ethers; D014753:Vinyl Compounds; C100195:vinyl ether