Tetrahedron Letters p. 3917 - 3920 (1995)
Update date:2022-09-26
Topics:
Willems, Johannes G. H.
An asymmetric catalytic synthesis of chiral amines using a chiral base catalysed [1,3]-proton shift reaction of imines is described. The isomerisation reaction of N-benzylimines 2a-b derived from prochiral ketones (benzylacetone, acetophenone) and p-substituted benzylamines, is catalysed by chiral alcohols and aminoalcohols 5-12 and gives enantiomerically enriched (up to 44% e.e.) N-benzylidene derivatives 3a-b. The resulting products 3a-b are readily hydrolysed to their corresponding amines 4a-b.
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