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. 2014 Aug 27;53(41):10925–10927. doi: 10.1002/anie.201406125

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© 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited

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Scheme 1 — BBOX catalyzes oxidative desymmetrization. A) BBOX catalyzes the stereoselective hydroxylation of γ-butyrobetaine (GBB) to (3R)-carnitine during carnitine biosynthesis. B) The BBOX-catalyzed oxidation of achiral N,N-dimethyl piperidine-4-carboxylic acid (1) gives (3R)-hydroxy-(4S)-N,N-dimethyl-piperidine-4-carboxylic acid (2). In the BBOX-catalyzed oxidation of a mixture of cis-N,N-ethylmethyl-piperidine-4-carboxylic acid (3 a) and trans-N,N-ethylmethyl-piperidine-4-carboxylic acid (3 b), only the cis isomer undergoes effective hydroxylation to give (3R)-hydroxy-(1R)-N,N-dimethyl-piperidine-(4S)-carboxylic acid (4 a).