One-step preparation of O-(α-bromoacyl) cyanohydrins by minor enantiomer recycling: Synthesis of 4-amino-2(5H)-furanones
2013 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 78, no 18, 9174-9180 p.Article in journal (Refereed) Published
O-(α-Bromoacyl) cyanohydrins were prepared in a single step from a range of different aldehydes in combination with α-bromoacyl cyanides. By the use of a cyclic procedure where the two minor diastereoisomers from a chiral Lewis acid-catalyzed reaction undergo Candida antarctica lipase B (CALB)-catalyzed hydrolysis followed by dehydrocyanation to regenerate the starting material, the products were obtained in good to high yields and in most cases with excellent diastereoselectivites. The synthetic importance of these compounds was demonstrated by the synthesis of 4-amino-2(5H)-furanones, a class of compounds that have shown both biological activity and utility as synthetic intermediates. This transformation was achieved by an intramolecular Blaise reaction, which gave the products in high to excellent yields and enantiomeric ratios.
Place, publisher, year, edition, pages
2013. Vol. 78, no 18, 9174-9180 p.
Candida antarctica lipase B, Diastereoisomers, Enantiomeric ratio, Furanones, High yield, Lewis acid-catalyzed reactions, Single-step, Synthetic intermediates
IdentifiersURN: urn:nbn:se:kth:diva-133262DOI: 10.1021/jo401401cISI: 000330159500026ScopusID: 2-s2.0-84884559931OAI: oai:DiVA.org:kth-133262DiVA: diva2:660631
FunderSwedish Research Council, 621-2012-3391
QC 201402242013-10-302013-10-292015-09-08Bibliographically approved