Resolution of Racemic 2-Aminocyclohexanol DeriVatiVes
additions of several nucleophiles to R-aminocarbonyls,13 ni-
troalkenes,14 imines,15 epoxides,11a,16 aziridines,11a,17 or cyclic
sulfates.18 Moreover, novel syntheses of vicinal amino alcohols
by enantioselective direct catalytic Mannich-type reactions were
recently reported by Trost, List, Barbas, and Shibasaki.19 Our
ongoing research in the fields of the catalytic enantioselective
aryl transfer to aldehydes,20 asymmetric sulfoxidation,7h,q-s and
desymmetrization of meso anhydrides21 is accompanied by the
interest in efficient syntheses of enantiopure â-amino alcohols
to enable an extensive ligand screening for the above-mentioned
reactions. In the anhydride opening project, two pseudoenan-
tiomeric cinchona alkaloids with â-amino alcohol units (quinine
and quinidine) proved to be highly stereoselective mediators in
the nucleophilic alcoholysis,22 and it has been shown that the
absolute configuration of the resulting hemiester correlates with
the configuration of the hydroxyl-bearing stereocenter of the
alkaloid.23 This relationship was also found in the diethylzinc
addition to aldehydes,24 which is of particular interest for our
studies because of the mechanistic analogies of the stereocontrol
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