Chiral Auxiliaries in the Vinyl Epoxide - Dihydrofuran Rearrangement

Synlett

Volumn 1996, Issue 4, 1996, Pages 401-403

  Batsanov, Andrei S ^a   Byerley, Andrew L J ^a   Howard, Judith A K ^a   Steel, Patrick G ^a  

^a DURHAM UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0010224013     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5418     Document Type: Article

References (13)

1. Hudlicky, T; Reed, J. W.; 'Rearrangements of Vinylcyclopropanes and Related Systems' in Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I.; Eds.;Vol 5 Ed. Paquette, L. A.; Pergamon: Oxford, 1991, pp928-936.
2. Eberbach, W.; Burchardt, B.; Chem. Ber., 1978, 111, 3665.
3. Crawford, R. J.; Lutener, S. B.; Cockroft, R. D.; Can. J. Chem., 1976, 54, 3364.
4. Bicyclic species, notably aziridines, have been employed in these rearrangements with high selectivity. See for example Hudlicky, T.; Seoane, G.; Price, J. D.; Gadamasetti, K.; Synlett, 1990, 433.
5. Payne, G. B.; J. Am. Chem. Soc., 1960, 82, 275.
6. Satisfactory physical and spectral data was obtained for all new compounds.
7. 2.
8. Ho, G-J.; Mathre, D. J.; J. Org. Chem.; 1995, 60; 2271.
9. Broker, C. A.; Ehrler, J.; Tetrahedron Lett., 1991, 5907.
10. +] = 336.1236.
11. 6b gives product ratios of: 48:43:5:4 in overall 68% yield. 6c and 6d give product ratios of: 57:33:6:4 in overall 68-72% yield.
12. 1 axes contain randomly disordered hexane molecules. Atomic co-ordinates, bond lengths and angles, and thermal parameters have been deposited at the Cambridge Crystallographic Data Centre; see Information for Authors, Issue No.1.
13. 7 gives product ratios of: 50:43:4:3 in overall 62% yield.