116836-35-2Relevant articles and documents
An amino alcohol ligand for highly enantioselective addition of organozinc reagents to aldehydes: Serendipity rules
Nugent, William A.
, p. 2133 - 2136 (2002)
(matrix presented) Amino alcohol 4 (or its enantiomer) is prepared in two simple steps. Commercial (1R,2S)-2-amino-1,2-diphenylethanol is dialkylated with bis(2-bromoethyl) ether. Subsequent hydrogenation over 5% Rh on alumina in the presence of morpholine unexpectedly stops at the hexahydro derivative 4. Amino alcohol 4 promotes the enantioselective addition of diethylzinc to aldehydes at room temperature in up to 99% enantiomeric excess.
Lipase/aluminum-catalyzed dynamic kinetic resolution of secondary alcohols
Berkessel, Albrecht,Sebastian-Ibarz, M. Luisa,Mueller, Thomas N.
, p. 6567 - 6570 (2006)
(Chemical Equation Presented) Racemization wanted: The dynamic kinetic resolution of secondary alcohols can be achieved by a simple and readily available catalyst system. Substrate racemization is effected at room temperature by a combination of (racemic) 1,1′-bi-2-naphthol (binol) or 2,2′-biphenol with AIMe3, and a lipase performs enantiospecific acylation (see scheme).
A stereoselective inverting sec -alkylsulfatase for the deracemization of sec -alcohols
Schober, Markus,Gadler, Petra,Knaus, Tanja,Kayer, Heidemarie,Birner-Gruenberger, Ruth,Guelly, Christian,MacHeroux, Peter,Wagner, Ulrike,Faber, Kurt
, p. 4296 - 4299 (2011/10/08)
A metallo-β-lactamase-type alkylsulfatase was found to catalyze the enantioselective hydrolysis of sec-alkylsulfates with strict inversion of configuration. This catalytic event, which does not have an analog in chemocatalysis, yields homochiral (S)-configurated alcohols and nonreacted sulfate esters. The latter could be converted into (S)-sec-alcohols as the sole product in up to >99% ee via a chemoenzymatic deracemization protocol on a preparative scale.
