Catalytic Asymmetric Allylboration of Indoles and Dihydroisoquinolines with Allylboronic Acids: Stereodivergent Synthesis of up to Three Contiguous Stereocenters
Number of Authors: 5
2016 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 55, no 46, 14415-14419 p.Article in journal (Refereed) Published
The catalytic asymmetric allylboration of cyclic imines with gamma,gamma-disubstituted allylboronic acids provides products with adjacent stereocenters in high yield and stereoselectivity. Various electrophiles, including 3,4-dihydroisoquinolines and indoles, were prenylated in a fully stereodivergent fashion by switching the E/Z geometry of the allylboronate and/or the enantiomer of the BINOL catalyst. 3-Methylindole provided products with three adjacent stereocenters with high stereoselectivity in one synthetic operation.
Place, publisher, year, edition, pages
2016. Vol. 55, no 46, 14415-14419 p.
allylboration, asymmetric catalysis, indoles, organocatalysis, stereoselectivity
IdentifiersURN: urn:nbn:se:su:diva-136262DOI: 10.1002/anie.201608605ISI: 000387028000040OAI: oai:DiVA.org:su-136262DiVA: diva2:1052356