Desymmetrization of cyclohexadienones via cinchonine derived thiourea-catalyzed enantioselective aza-Michael reaction and total synthesis of (-)-Mesembrine.
DOI Number:
10.1039/c1sc00083g
Reaction Category:
RXNO ID:
RXNO_0000009
Educt:
N-(2-((4'-fluoro-4-oxo-[1,1'-biphenyl]-1(4H)-yl)oxy)ethyl)-4-methylbenzenesulfonamide (cyclohexadienones)
Product:
(4S,4aS,8aS)-8a-(4-fluorophenyl)-4-tosyl-3,4,4a,8a-tetrahydro-2H-4lambda4-benzo[b][1,4]oxazin-6(5H)-one (morpholine derivative)
Catalyst:
1-(3,5-bis(trifluoromethyl)phenyl)-3-((R)-quinolin-4-yl((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methyl)thiourea
Cas No:
851477-19-5
Associated Product from Buchler GmbH:
Cinchonine Base
Cas No:
118-10-5