Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 46, Pages 14415-14419Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201608605
Keywords
allylboration; asymmetric catalysis; indoles; organocatalysis; stereoselectivity
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Funding
- Swedish Research Council
- Knut och Alice Wallenbergs Foundation
- Erasmus fellowship (EU)
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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.
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