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.
Terada
Masahiro
M
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan.
Toda
Yasunori
Y
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