Enzyme-promoted desymmetrization of bis (2-hydroxymethylphenyl) sulfoxide as a route to tridentate chiral catalysts

…, WM Wieczorek, M Szyrej, L Sieroń, P Kiełbasiński

Index: Rachwalski, Michal; Kwiatkowska, Malgorzata; Drabowicz, Jozef; Klos, Marcin; Wieczorek, Wanda M.; Szyrej, Malgorzata; Sieron, Leslaw; Kielbasinski, Piotr Tetrahedron Asymmetry, 2008 , vol. 19, # 17 p. 2096 - 2101

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Citation Number: 30

Abstract

The desymmetrization of prochiral bis (2-hydroxymethylphenyl) sulfoxide 3 was efficiently performed via acetylation promoted by commonly available lipases. Two lipases, namely, CAL-B and LPL proved particularly efficient to give 2-acetoxymethylphenyl 2- hydroxymethylphenyl sulfoxide 4 in up to 98% yield and with up to 98% ee. On the basis of an X-ray analysis, the absolute configuration of 4 was determined as (+)-(R). The ...