Asymmetric copper-catalysed alkene cyclopropanation and aziridination using tartrate-derived bis-oxazoline ligands

Tetrahedron Letters

Volumn 37, Issue 34, 1996, Pages 6189-6192

  Harm, Andrew M ^b   Knight, Julian G ^b   Stemp, Geoffrey ^a  

^a GLAXOSMITHKLINE   (United Kingdom)

^b NEWCASTLE UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; OXAZOLINE DERIVATIVE; STYRENE;

ARTICLE; CONFORMATIONAL TRANSITION; DRUG CONFORMATION; ENANTIOMER; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0000763618     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01320-2     Document Type: Article

References (12)

1. 1. Doyle, M.P. Rec. Trav. Chim. Pays-Bas, 1991,110, 305
2. 2. Doyle, M.P.; Austin, R.E.; Bailey, A.S.; Dwyer, M.P.; Dyatkin, A.B.; Kalinin, A.V.; Kwan, M.Y.; Liras, S.; Oalmann, C.J.; Pieters, R.J.; Protopopova, M.N.; Raab, C.E.; Roos, G.H.P.; Zhou, Q.-L.; Martin, S.F. J. Am. Chem. Soc., 1995, 117, 5763
3. 3. Evans, D.A.; Woerpel, K.A.; Hinman, M.M.; Faul, M.M. J. Am. Chem. Soc., 1991, 113, 726
4. 4. Lowenthal, R.E.; Masamune, S. Tetrahedron Lett., 1991, 32, 7373
5. 5. For an account of the mechanism of enantioselective cyclopropanation see: Fritschi, H.; Leutenegger, U.; Pfaltz, A. Helv. Chim. Acta, 1988, 71, 1553.
6. 6. Evans, D.A.; Faul, M.M.; Bilodeau, M.T.; Anderson, B.A.; Barnes, D.M. J. Am. Chem. Soc., 1993, 115, 5328
7. 7. Li, Z.; Conser, K.R.; Jacobsen, E.N. J. Am. Chem. Soc., 1993, 115, 5326
8. 8. Noda, K.; Hosoya, N.; Irie, R.; Ito, Y.; Katsuki, T. Synlett, 1993, 469
9. 9. Tanner, D. Angew. Chem., Int. Ed. Engl., 1994, 33, 599.
10. 10. Harm, A.M.; Knight, J.G.; Stemp, G. Synlett, 1996, in press.
11. 11. Li, Z.; Quan, R.W.; Jacobsen, E.N. J. Am. Chem. Soc., 1995, 117, 5889.
12. + + H, 5%), 309 (20), 267 (25), 223 (55), 154 (100), and 43 (80). The identity of this compound was confirmed by X-ray crystal structure determination.