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Enantioenriched Acylated Cyanohydrins: Synthesis and Analysis
KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.ORCID-id: 0000-0002-1743-7650
2010 (engelsk)Inngår i: Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, ISSN 0936-5214, E-ISSN 1437-2096, nr 3, s. 355-367Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

The addition of acyl cyanides to prochiral aldehydes catalyzed by a chiral Lewis acid and an achiral Lewis base produces highly enantioenriched O-acylated cyanohydrins. alpha-Keto esters undergo the same type of addition, although via a different mechanism in which the enantioselectivity originates from a chiral Lewis base. In the presence of a biocatalyst, the minor, undesired enantiomer obtained in the reactions with aldehydes can be selectively hydrolyzed to re-form the starting aldehyde, permitting the reaction to be run in a cyclic manner. The minor-enantiomer recycling results in an essentially enantiopure product. Selective enzymatic hydrolysis is also a key step in high-throughput analysis of conversions and enantiomeric ratios.

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2010. nr 3, s. 355-367
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URN: urn:nbn:se:kth:diva-19174DOI: 10.1055/s-0029-1219154ISI: 000274233900002Scopus ID: 2-s2.0-76349100717OAI: oai:DiVA.org:kth-19174DiVA, id: diva2:337221
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QC 20100525Tilgjengelig fra: 2010-08-05 Laget: 2010-08-05 Sist oppdatert: 2017-12-12bibliografisk kontrollert

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