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Catalytic Asymmetric Allylboration of Indoles and Dihydroisoquinolines with Allylboronic Acids: Stereodivergent Synthesis of up to Three Contiguous Stereocenters
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
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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
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.

Place, publisher, year, edition, pages
2016. Vol. 55, no 46, 14415-14419 p.
Keyword [en]
allylboration, asymmetric catalysis, indoles, organocatalysis, stereoselectivity
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-136262DOI: 10.1002/anie.201608605ISI: 000387028000040OAI: oai:DiVA.org:su-136262DiVA: diva2:1052356
Available from: 2016-12-06 Created: 2016-12-01 Last updated: 2016-12-06Bibliographically approved

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