Tetrahedron Asymmetry p. 1773 - 1789 (1997)
Update date:2022-08-04
Topics:
Ostendorf, Martin
Romagnoli, Romeo
Pereiro, Isabel Cabeza
Roos, Eric C.
Moolenaar, Marinus J.
Speckamp, W. Nico
Hiemstra, Henk
Full details of the enantioselective reduction of cyclic meso-imides catalysed by an enantiopure oxazaborolidine derived from (S)-α,α-diphenylprolinol are reported. Treatment of the imides with borane in the presence of the catalyst led to a mixture of cis- and trans-hydroxylactams and, after subsequent ethanolysis, to the corresponding diastereomerically pure trans-ethoxylactams. The enantiomeric excesses were shown to be 68-94% by HPLC-determination. One example, in which the ethoxylactam was converted into the benzenesulfonyllactam, could be crystallized to >99% enantiomeric purity.
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Doi:10.1039/a702802d
(1997)Doi:10.1007/s00706-010-0341-1
(2010)Doi:10.1016/S0960-894X(97)00337-5
(1997)Doi:10.1021/ja00408a034
(1981)Doi:10.1016/j.bmcl.2004.02.068
(2004)Doi:10.1039/a703164e
(1997)