New Tartrate-Derived Bis-Oxazoline Ligands for Enantioselective Cyclopropanation and Aziridination of Alkenes

Synlett

Volumn 1996, Issue 7, 1996, Pages 677-678

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

^a NEWCASTLE UNIVERSITY   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0038089180     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5563     Document Type: Article

References (19)

1. a. Doyle, M.P. Rec. Trav. Chim. Pays-Bas, 1991, 110, 305;
2. b. 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. c. Evans, D.A.; Woerpel, K.A.; Hinman, M.M.; Faul, M.M. J. Am Chem Soc., 1991, 113, 726;
4. d. Lowenthal, R.E.; Masamune, S. Tetrahedron Lett., 1991, 32, 7373.
5. a. Evans, D.A.; Faul, M.M.; Bilodeau, M.T.; Anderson, B.A.; Barnes, D.M. J. Am. Chem. Soc., 1993, 115, 5328;
6. b. Li, Z.; Conser, K.R.; Jacobsen, E.N. J. Am. Chem Soc., 1993, 115, 5326;
7. c. Noda, K.; Hosoya, N.; Irie, R.; Ito, Y.; Katsuki, T. Synlett, 1993, 469;
8. d. Tanner, D. Angew Chem., Int. Ed. Engl., 1994, 33, 599.
9. For a leading reference see: Hayashi, T.; Ohno, A.; Lu, S.-J.; Matsumoto, Y.; Fukuyo, E.; Yanagi, K. J. Am. Chem. Soc., 1994, 116, 4221.
10. Davies, I.W.; Senanayake, C.H.; Larsen, R.D.; Verhoeven, T.R.; Reider, P.J. Tetrahedron Lett., 1996, 37, 813 and references therein.
11. Jacobsen, E.N.; Zhang, W.; Muci, A.R.; Ecker, J.R.; Deng, L. J. Am. Chem. Soc., 1991, 113, 7063.
12. For a review of this type of oxazoline synthesis see: Frump, J.A. Chem. Rev, 1971, 71, 483.
13. Dodd, J.H.; Guan, J.; Schwender, C.E. Synth. Commun., 1993, 23, 1003.
14. 6 requires: C, 64.47; H, 6.59; N, 6.54; Found: C, 64.47; H, 6.56; N, 6.42.
15. Lafargue, P.; Guenot, P.; Lellouche, J.-P. Heterocycles, 1995, 41, 947.
16. 3): 377.1501; Found: 377.1495.
17. Li, Z.; Quan, R.W.; Jacobsen, E.N. J. Am. Chem. Soc., 1995, 117, 5889.
18. For an account of the mechanism of enantioselective cyclopropanation see: Fritschi, H.; Leutenegger, U.; Pfaltz, A. Helv Chim Acta, 1988, 71, 1553.
19. 12