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

Autor:	Siavosh Mahboobi, Klaus Noack, Karl Bernauer, Peter Schönholzer, Ralf Freund
Rok vydání:	1990
Předmět:	Steric effects chemistry.chemical_classification Aldimine Bicyclic molecule Stereochemistry Organic Chemistry Crystal structure Biochemistry Catalysis Tryptamines Inorganic Chemistry chemistry Drug Discovery Alkoxy group Molecule Physical and Theoretical Chemistry Tricyclic
Zdroj:	Helvetica Chimica Acta. 73:439-454
ISSN:	0018-019X
Popis:	C-(Alkoxycarbonyl)formimines of type 15–18 were derived from the 2-substituted tryptamines 2, 9, 10, and 11 and transformed with tosyl chloride into tricyclic 3-spiroindoles of types 19–22 (Scheme 3). The influence of the homochiral alkoxy moieties A–D on the stereochemical outcome of this reaction was studied. Good-to-excellent diastereoselectivities were observed with the (−)-8-(phenylmenth-3-yl)oxy group (B) as homochiral auxiliary. The structures of the tricycles 4, (2′R,3S)-19B, and (2′S,3R)20C were established by X-ray analysis, the structures of the others by NOE and CD studies, and by chemical correlation. Possibilities to explain the steric course of the spirocyclizations are discussed.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::2f76b916df45a6a5b3ecf366fe9a66b2 https://doi.org/10.1002/hlca.19900730224 Zobrazit plný text záznamu Plný text