Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 21, Pages 10214-10226Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b01047
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Funding
- Ministerio de Ciencia e Innovacion (MCINN) [CTQ2010-20387, CONSOLIDER INGENIO 2010-CDS2007-00006, CTQ2011-24165]
- Ministerio de Economia y Competitividad (MINECO) [CTQ2014-53695-P, CTQ2014-51912-REDC]
- FEDER
- Generalitat Valenciana [PROMETEO 2009/039, PROMETEOII/2014/017]
- University of Alicante
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The addition of an allenyl indium intermediate to chiral N-tert-butanesulfinyl imines 7 proceeds with high levels of diaster-eocontrol. The resulting homopropargylic amine derivatives 10 were transformed into 2-(2-aminoalkyl)benzofuran and indole derivatives 13 and 19, after Sonogashira coupling with o-iodophenol or o-iodoaniline, followed by formation of the heteroaromatic ring through an intramolecular cyclization. Enantioenriched tetrahydropyrido-benzofuran and indole derivatives 16 and 21 were prepared through a Pictet-Spehgler condensation of the free amines derived from compounds 15 and 20, involving the nudeophilic 3-position of the benzofuran or indole moiety.
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