Selective Formation of Adjacent Stereocenters by Allylboration of Ketones under Mild Neutral Conditions
2013 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 15, no 10, 2546-2549 p.Article in journal (Refereed) Published
Allylboronic acids readily react with a broad variety of ketones, affording homoallylic alcohols with adjacent quaternary and tertiary stereocenters. The reaction proceeds with very high anti stereoselectivity even if the substituents of the keto group have a similar size. a-Keto acids react with syn stereoselectivity probably due to the formation of acyl boronate intermediates. The allylation reactions proceed without added acids/bases under mild conditions. Because of this, many functionalities are tolerated even with in situ generated allylboronic acids.
Place, publisher, year, edition, pages
2013. Vol. 15, no 10, 2546-2549 p.
Research subject Organic Chemistry
IdentifiersURN: urn:nbn:se:su:diva-91841DOI: 10.1021/ol401055mISI: 000319720900056OAI: oai:DiVA.org:su-91841DiVA: diva2:636002
FunderThe Wenner-Gren FoundationSwedish Research CouncilKnut and Alice Wallenberg Foundation