Practical Proline-catalyzed asymmetric Mannich reaction of aldehydes with N-Boc-imines.
This protocol describes a procedure for the synthesis of alpha, beta-branched-b-amino aldehydes via Proline-catalyzed asymmetric Mannich reaction of aldehydes with N-tert-butoxycarbonyl-imines. The crystalline beta-amino aldehydes are formed in good yields and extremely high levels of diastereo- and enantioselectivities without the need for chromatographic purification and are readily oxidized to the corresponding beta-amino acids. The protocol can be completed in approximately 14 h on small scales or up to 30 h on larger scales.
Yang
Jung Woon
JW
Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany.
Stadler
Michael
M
List
Benjamin
B
D000097:Acetonitriles / Q000737:chemistry; D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D001547:Benzaldehydes / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D005563:Formic Acid Esters / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D011392:Proline / Q000737:chemistry*
D000097:Acetonitriles; D000447:Aldehydes; D001547:Benzaldehydes; D005563:Formic Acid Esters; D007097:Imines; C000345:t-butyloxycarbonyl group; C010463:n-hexanal; D011392:Proline; C032175:benzaldehyde; C032159:acetonitrile