ISSN:
0018-019X
Schlagwort(e):
Chemistry
;
Organic Chemistry
Quelle:
Wiley InterScience Backfile Collection 1832-2000
Thema:
Chemie und Pharmazie
Notizen:
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.
Zusätzliches Material:
6 Ill.
Materialart:
Digitale Medien
URL:
http://dx.doi.org/10.1002/hlca.19900730224
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