Stereocontrol in Synthesis of Homoallylic Amines. Syn Selective Direct Allylation of Hydrazones with Allylboronic Acids
2014 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 16, no 14, 3808-3811 p.Article in journal (Refereed) Published
Allylboronic acids directly react with acyl hydrazones, affording homoallylic amine derivatives. The reaction proceeds with very high syn selectivity, which is the opposite of the stereochemistry observed for allylboration of imines. The reaction can be carried out with both aromatic and aliphatic acyl hydrazones. Based on our studies the excellent syn stereochemistry can be explained by chelation control of the acyl hydrazone and the B(OH)(2) moiety.
Place, publisher, year, edition, pages
2014. Vol. 16, no 14, 3808-3811 p.
Research subject Organic Chemistry
IdentifiersURN: urn:nbn:se:su:diva-106905DOI: 10.1021/ol501699xISI: 000339367300050OAI: oai:DiVA.org:su-106905DiVA: diva2:741227
FunderSwedish Research CouncilKnut and Alice Wallenberg Foundation