Preparation of (R)-(1-adamantyl)glycine and (R)-2-(1-adamantyl)-2-aminoethanol: a combination of cobalt-mediated beta-ketoester alkylation and enzyme-based aminoalcohol resolution

Alkylation of the cobalt(II) complex of ethyl acetoacetate with 1-bromoadam antane affords ethyl 2-(1-adamantyl)acetoacetate, which was converted into rac-(1-adamantyl)glycine 1 and rac-2-(1-adamantyl)-2-aminoethanol 7. This w as separated into enantiomers by means of vinyl acetate in the presence of Pseudomonas cepacea. Configuration R was assigned to the enantiomerically p ure aminoalcohol (R)-7 on the basis of X-ray diffraction data. Further oxid ation of N-protected aminoalcohol (R)-8 afforded enantiomerically pure amin o acid (R)-1. (C) 2000 Elsevier Science Ltd. All rights reserved.