Stereoselective Synthesis of 2‑(2-Aminoalkyl)- and 1,3-Disubstituted Tetrahydro‑1H‑pyrido[4,3‑b]- Benzofuran and Indole Derivatives

The addition of an allenyl indium intermediate to chiral N-tert-butanesulfinyl imines 7 proceeds with high levels of diastereocontrol. The resulting homopropargylic amine derivatives 10 were transformed into 2-(2-aminoalkyl)­benzofuran and indole derivatives 13 and 19, after Sonogashira coupling wit...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 81; no. 21; pp. 10214 - 10226
Main Authors García-Muñoz, María Jesús, Foubelo, Francisco, Yus, Miguel
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.11.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ROUTE
TERT-BUTANESULFINYL IMINES
ASYMMETRIC-SYNTHESIS
PROPARGYLATION
AMINES
CONDENSATION
SEROTONIN
ALDEHYDES
DIASTEREOSELECTIVE ADDITION
ANTAGONISTS
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Summary:The addition of an allenyl indium intermediate to chiral N-tert-butanesulfinyl imines 7 proceeds with high levels of diastereocontrol. 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-Spengler condensation of the free amines derived from compounds 15 and 20, involving the nucleophilic 3-position of the benzofuran or indole moiety.
Bibliography:ObjectType-Article-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b01047