3-aza-Cope rearrangement of quaternary N-allyl enammonium salts. Stereospecific 1,3 allyl migration from nitrogen to carbon on a tricyclic template

Journal of Organic Chemistry

Volumn 65, Issue 16, 2000, Pages 4938-4943

  McComsey, David F ^a   Maryanoff, Bruce E ^a  

^a R W JOHNSON PHARMACEUTICAL RES I   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AMMONIUM DERIVATIVE; DEUTERIUM; ENAMINE; ISOQUINOLINE DERIVATIVE; NITROGEN; PYRROLO[2,1 ALPHA]ISOQUINOLINE; QUINOLIZINE DERIVATIVE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; MIGRATION; PROTON TRANSPORT; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0034637491     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000363h     Document Type: Article

References (33)

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28. 1H NMR spectrum of 19 showed a small doublet at δ 3.97 (J = 7.0 Hz) for ca. 6% protio species at the beginning of the rearrangement study.
29. (a) Hrovat, D. A. Beno, B. R.; Lange, H.; Yoo, H.-Y.; Houk, K. N.; Borden, W. T. J. Am. Chem. Soc. 1999, 121, 10529-10537 and references therein.
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33. A two-step, diradical mechanism has been evoked for a Cope rearrangement in a strained polycyclic system, see: Roth, W. R.; Gleiter, R.; Paschmann, V.; Hackler, U. E.; Fritzsche, G.; Lange, H. Eur. J. Org. Chem. 1998, 961-967. Also, see ref 9c.