Tandem 1,3-azaprotio cyclotransfer-cycloaddition reactions between ketoximes and divinyl ketone or its equivalents: Lewis acid mediated rate enhancement and control of cycloaddition regioselectivity

Tetrahedron Letters

Volumn 38, Issue 34, 1997, Pages 6099-6102

  Saba, Imaad S ^a   Frederickson, Martyn ^a   Grigg, Ronald ^a   Dunn, Peter J ^b   Levett, Philip C ^b  

^a UNIVERSITY OF LEEDS   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO[3.2.1]OCTANE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030744312     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01377-4     Document Type: Article

References (13)

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4. Grigg, R.; Dorrity, M.J.; Heaney, F.; Malone, J.F.; Rajviroongit, S.; Sridharan, V.; Surendrakumar, S. Tetrahedron, 1991, 47, 8297-8322.
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8. 1H nmr and m/z) and microanalytical data.
9. 2] with nitrones [e.g. Sawitzki, G.; von Schnering, H.G. Chem. Ber., 1974, 107, 3266-3274] and there is also strong evidence for many organozinc species existing as dimeric or polymeric species in solution [e.g. Reformatsky reagents: Dekker, J.; Budzelaar, P.H.M.; Boersma, J.; van der Kerk, G.J.M.; Spek, A.L. Organometallics, 1984, 3, 1403-1407].
10. 2] with nitrones [e.g. Sawitzki, G.; von Schnering, H.G. Chem. Ber., 1974, 107, 3266-3274] and there is also strong evidence for many organozinc species existing as dimeric or polymeric species in solution [e.g. Reformatsky reagents: Dekker, J.; Budzelaar, P.H.M.; Boersma, J.; van der Kerk, G.J.M.; Spek, A.L. Organometallics, 1984, 3, 1403-1407].
11. Kanemasa, S.; Uemura, T.; Wada, E. Tetrahedron Lett., 1992, 33, 7889-7892.
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13. Kanemasa, S.; Tsuruoka, T.; Yamamoto, H. Tetrahedron Lett., 1995, 36, 5019-5022.