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Please login or sign up for a free trial to access the full content. Variation 1: Enzymatic Kinetic Resolution

DOI: 10.1055/sos-SD-040-00265

Azov, V. A.Science of Synthesis, (200940421.

In contrast to selective enzymatic acylation and deacylation of alcohols, which has become an effective and widespread technique for the preparation of optically enriched compounds in laboratory practice and in industry, the corresponding enzymatic kinetic resolution of amines is less developed. This disparity originates from two fundamental differences between alcohol and amine resolution: (1) due to the higher nucleophilicity of amines, blank nonenzymatic acylation should be taken into account; (2) hydrolysis of the acylated product is much more difficult in the case of amides compared to esters. Nevertheless, significant progress has been made in the enantioselective enzymatic acylation of amines since the early 1990s (for a review on kinetic enzymatic resolution of amines see ref[‌11‌]) and this has paved the way for a practical application of the method, even on a multiton industrial scale with production capacity of up to 2500 tons per year achieved by BASF in the resolution of rac-1-methoxypropan-2-amine.[‌10‌]

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