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Translation: Chiralcel IC-H column [ = 230 nm; eluent: Hexane/Isopropanol = 80/20; Flow rate: allyl bromide (1.2 equiv) was added. The reaction mixture was stirred at 0 °C for another -
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77 (s, 1H), 5.14-5.18 (m, 2H), 5.23 (dd, J 1 = 1.2 Hz, J 2 = 17.2 Hz, 1H), 5.41 (dd -
HRMS (ESI) calcd. for C 35 H 37 N 2 O 3 S (M+H) + : 565.2519, Found: 565.2511. Enantiomeric excess was determined by HPLC with a Chiralcel IC-H column [ = 230 nm -
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58 (m, 1H), 6.72 (d, J = 2.8 Hz, 1H) 6 -
Empirical Formula: C 30 H 32 N 2 O 3 S; Formula Weight: 500.63; Crystal Color, Habit: colorless; Crystal Dimensions: 0.200 x 0.110 x 0.080 mm 3 ; Crystal System: Monoclinic -
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- Publisher
- Royal Society of Chemistry
- Copyright
- This journal is © The Royal Society of Chemistry
- ISSN
- 2041-6520
- DOI
- 10.1039/c8sc01595c
- Publisher site
- See Article on Publisher Site
Abstract
We reported a highly regio- and enantioselective hydroamination and hydroindolation of keto-vinylidenecyclopropanes via cationic Rh(i) catalysis in this context. The combination of various secondary amines and indoles with keto-vinylidenecyclopropanes afforded the corresponding hydrofunctionalization products in good to excellent yields with outstanding ee values under mild conditions. A new TMMRh model complex was proposed, providing an atom economical Rh--allyl precursor at the same time. Moreover, the resulting products could easily be transformed into more complex polyheterocycles upon further synthetic manipulation.
Journal
Chemical Science – Royal Society of Chemistry
Published: May 18, 2018