Stereoselective allylboration of imines and indoles under mild conditions. An in situ E/Z isomerization of imines by allylboroxines
Number of Authors: 6
2014 (English)In: Chemical Science, ISSN 2041-6520, E-ISSN 2041-6539, Vol. 5, no 7, 2732-2738 p.Article in journal (Refereed) Published
Direct allylboration of various acyclic and cyclic aldimine, ketimine and indole substrates was performed using allylboronic acids. The reaction proceeds with very high anti-stereoselectivity for both E and Z imines. The allylboroxines formed by dehydration of allylboronic acids have a dual effect: promoting E/Z isomerization of aldimines and triggering the allylation by efficient electron withdrawal from the imine substrate.
Place, publisher, year, edition, pages
2014. Vol. 5, no 7, 2732-2738 p.
Research subject Organic Chemistry
IdentifiersURN: urn:nbn:se:su:diva-106118DOI: 10.1039/c4sc00415aISI: 000337108200016OAI: oai:DiVA.org:su-106118DiVA: diva2:735014
FunderSwedish Research CouncilKnut and Alice Wallenberg Foundation