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Catalytic Asymmetric Allylboration of Indoles and Dihydroisoquinolines with Allylboronic Acids: Stereodivergent Synthesis of up to Three Contiguous Stereocenters
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för material- och miljökemi (MMK).
Vise andre og tillknytning
2016 (engelsk)Inngår i: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 55, nr 46, s. 14417-14421Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

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.

sted, utgiver, år, opplag, sider
2016. Vol. 55, nr 46, s. 14417-14421
Emneord [en]
allylboration, asymmetric catalysis, indoles, organocatalysis, stereoselectivity
HSV kategori
Identifikatorer
URN: urn:nbn:se:su:diva-136262DOI: 10.1002/anie.201608605ISI: 000387028000040OAI: oai:DiVA.org:su-136262DiVA, id: diva2:1052356
Forskningsfinansiär
Swedish Research CouncilKnut and Alice Wallenberg FoundationTilgjengelig fra: 2016-12-06 Laget: 2016-12-01 Sist oppdatert: 2017-05-27bibliografisk kontrollert

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Alam, RaufulDiner, ColinJonker, SybrandEriksson, LarsSzabó, Kálmán J.
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