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Enantioenriched Acylated Cyanohydrins: Synthesis and Analysis
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.ORCID iD: 0000-0002-1743-7650
2010 (English)In: Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, ISSN 0936-5214, E-ISSN 1437-2096, no 3, 355-367 p.Article in journal (Refereed) 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.

Place, publisher, year, edition, pages
2010. no 3, 355-367 p.
URN: urn:nbn:se:kth:diva-19174DOI: 10.1055/s-0029-1219154ISI: 000274233900002ScopusID: 2-s2.0-76349100717OAI: diva2:337221
QC 20100525Available from: 2010-08-05 Created: 2010-08-05Bibliographically approved

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Moberg, Christina
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