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Issue 2, 2017
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Asymmetric synthesis of (S)-phenylacetylcarbinol – closing a gap in C–C bond formation

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Abstract

(S)-Phenylacetylcarbinol [(S)-PAC] and its derivatives are valuable intermediates for the synthesis of various active pharmaceutical ingredients (APIs), but their selective synthesis is challenging. As no highly selective enzymes or chemical catalysts were available, we used semi-rational enzyme engineering to tailor a potent biocatalyst to be >97% stereoselective for the synthesis of (S)-PAC. By optimizing the reaction and process used, industrially relevant product concentrations of >48 g L−1 (up to 320 mM) were achieved. In addition, the best enzyme variant gave access to a broad range of ring-substituted (S)-PAC derivatives with high stereoselectivity, especially for meta-substituted products.

Graphical abstract: Asymmetric synthesis of (S)-phenylacetylcarbinol – closing a gap in C–C bond formation

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Publication details

The article was received on 01 Jul 2016, accepted on 17 Oct 2016 and first published on 17 Oct 2016


Article type: Communication
DOI: 10.1039/C6GC01803C
Citation: Green Chem., 2017,19, 380-384
  • Open access: Creative Commons BY license
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    Asymmetric synthesis of (S)-phenylacetylcarbinol – closing a gap in C–C bond formation

    T. Sehl, S. Bock, L. Marx, Z. Maugeri, L. Walter, R. Westphal, C. Vogel, U. Menyes, M. Erhardt, M. Müller, M. Pohl and D. Rother, Green Chem., 2017, 19, 380
    DOI: 10.1039/C6GC01803C

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