Hydrolysis of iminium ethers derived from the reaction of ketones with hydroxy azides: Synthesis of macrocyclic lactams and lactones

Journal of Organic Chemistry

Volumn 64, Issue 12, 1999, Pages 4381-4385

  Forsee, Jennifer E ^a   Aubé, Jeffrey ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; ALCOHOL; AZIDE; CYCLOHEPTANE DERIVATIVE; CYCLOHEXANONE; ETHER DERIVATIVE; IMINE; KETONE; LACTAM; LACTONE; MACROCYCLIC COMPOUND; MACROLIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROLYSIS; PROTON TRANSPORT; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033546244     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990041h     Document Type: Article

References (14)

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2. For reviews of early work with iminium ethers, see: (a) Hünig, S. Angew. Chem., Int. Ed. Engl. 1964, 3, 548-560. (b) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: Oxford, 1983; pp 101-162.
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12. For some recent examples, see: (a) Gribble, G. W.; Silva, R. A. Tetrahedron Lett. 1996, 37, 2145-2148. (b) Derrer, S.; Feeder, N.; Teat, S. J.; Davies, J. E.; Holmes, A. B. Tetrahedron Lett. 1998, 39, 9309-9312. (c) Banfi, L.; Guanti, G.; Rasparini, M. Tetrahedron Lett. 1998, 39, 9539-9542.
13. For some recent examples, see: (a) Gribble, G. W.; Silva, R. A. Tetrahedron Lett. 1996, 37, 2145-2148. (b) Derrer, S.; Feeder, N.; Teat, S. J.; Davies, J. E.; Holmes, A. B. Tetrahedron Lett. 1998, 39, 9309- 9312. (c) Banfi, L.; Guanti, G.; Rasparini, M. Tetrahedron Lett. 1998, 39, 9539-9542.
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