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Diastereoselective Spirocyclization of Imines of 2-Substituted 1H-Indole-3-ethylamines ( = Trypatamines): Variation of the electrophile and the substituent at C(2) and its influence on the steric outcome. 6th Communication on indoles, indolenines, and indolines

✍ Scribed by Ralf Freund; Suzanna Martinović; Karl Bernauer

Book ID: 102257369
Publisher: John Wiley and Sons
Year: 1992
Tongue: German
Weight: 337 KB
Volume: 75
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19920750124

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✦ Synopsis

Recently, we reported on the spirocyclization of C-(alkoxycar-bony1)formimines 2 of 2-substituted tryptamines 1 by TsCl as electrophile in the presence Scheme I

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Diastereoselective Spirocyclization of C-(Alkyloxycarbonyl)formimines of 2-Substituted 1HIndole-3-ethanamines (= Tryptamines): Basic Studies. 5th Communication on Indoles, Indolenines, and Indolines

✍ Ralf Freund; Siavosh Mahboobi; Klaus Noack; Peter Schonhölzer; Karl Bernauer 📂 Article 📅 1990 🏛 John Wiley and Sons 🌐 German ⚖ 955 KB

## OMe H OMe ') 4th communication: [I] . ## H COOMe (2'S,3R)-20 23 (-)-Tabersonine The imine 15B afforded, with good diastereoselectivity, the crystalline (2'R,3S)-tricycle 19B. In the case of 15D, a crystalline mixture of diastereoisomers 19D was obtained. With the imine 17B, again formation o