Ring expansion of functionalized octahydroindoles to enantiopure cis-decahydroquinolines

Journal of Organic Chemistry

Volumn 71, Issue 16, 2006, Pages 5930-5935

  Mena, Marisa ^a   Bonjoch, Josep ^a   Pardo, Domingo Gomez ^b   Cossy, Janine ^b  

^a UNIVERSITY OF BARCELONA   (Spain)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; ISOMERS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

CIS-DECAHYDROQUINOLINES; OCTAHYDROINDOLES; RING EXPANSION;

NITROGEN COMPOUNDS;

1 BENZYL 2 (HYDROXYMETHYL)OCTAHYDROINDOL 6 ONE ETHYLENE ACETAL; DECAHYDROQUINOLINE DERIVATIVE; INDOLE DERIVATIVE; OCTAHYDROINDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CIS ISOMER; ENANTIOMER; PRODUCT RECOVERY; REACTION ANALYSIS; RING OPENING;

EID: 33746876014     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060592p     Document Type: Article

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48. 13C NMR spectrum of the reaction mixture. For NMR data of 9b-12b, see Supporting Information. (Diagram presented)
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51. The use of silver trifluoroacetate instead of silver acetate slightly increased the yield of the expanded compound, which gave alcohol 21 (58%) after a basic workup (see Scheme 6).
52. The use of tetrabutylammonium acetate did not improve the course of the reaction. From 9a, a mixture of acetates 17 (38%) and 9c (34%) were isolated, whereas from 10a-12a, more complex reaction mixtures were formed with the decahydroquinolines 18, 19, and 20 being obtained in a yield lower than 10%.