CHEMIOENZYMA SYNTHESIS OF ENANTIOPURE DERIVATIVES OF 3-AMINOINDAN-1-OL AND INDANO-1,3-DIAMINE

摘要

Chemoenzymatic synthesis of enantiopide derivatives of 3-aminoindan-1-ol and indane-1,3-diamine. Said process consists of the enantioselective acylation catalyzed by hydrolases, mainly lipases in organic media, of the hydroxyl groups of the aforementioned amino alcohols. The best biocatalyst is Candida antarctica lipase and the most effective acylating agent is vinyl acetate. Thus, the configuration enantiopide aminoindanes (1S, 3S) and (1S, 3R) and the corresponding acetylated configuration products (1R, 3R) and (1R, 3S) can be obtained. The corresponding analog diamines, products of great interest for their potent neuroprotective activity, have been prepared efficiently and in a single step from the enantiopide aminoindanols obtained by this methodology. The selective deprotection of the amino groups of the enantiopure diamines obtained is also described.