Issue 2, 2017

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

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

Supplementary files

Article information

Article type
Communication
Submitted
01 Jul 2016
Accepted
17 Okt 2016
First published
17 Okt 2016
This article is Open Access
Creative Commons BY license

Green Chem., 2017,19, 380-384

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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