Asymmetric rearrangement of N-Boc 7-azanorbornene oxide: Use of aryllithiums for enantioselective deprotonation

Tetrahedron Asymmetry

Volumn 10, Issue 10, 1999, Pages 1847-1850

  Hodgson, David M ^a   Maxwell, Christopher R ^a   Matthews, Ian R ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; N 7 AZANORBORNENE OXIDE; NORBORNENE DERIVATIVE; OXAZOLINE DERIVATIVE; SPARTEINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ENANTIOMER; PRIORITY JOURNAL; PROTON TRANSPORT;

EID: 0033591124     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00168-8     Document Type: Article

References (15)

1. Hodgson, D. M.; Maxwell, C. R.; Matthews, I. R. Synlett 1998, 1349-1350.
2. Isolated total yields of chromatographically homogeneous, spectroscopically pure products are reported. Ees were determined on the 2,4-dinitrobenzoate derivative by HPLC [Daicel Chiralpak AD column, 30:70 EtOH/hexane as eluent].
3. Hodgson, D. M.; Lee, G. P.; Marriott, R. E.; Thompson, A. J.; Wisedale, R.; Witherington, J. J. Chem. Soc., Perkin Trans. 1 1998, 2151-2161.
4. 3)}; a study of this process will be reported in due course. Such cyclohexenol products were not observed using substituted aryllithiums/4 (or in the reactions reported in Table 2).
5. 4 reduction followed by Boc protection (Arakawa, Y.; Yasuda, M.; Ohnishi, M.; Yoshifuji, S. Chem. Pharm. Bull. 1997, 45, 255-259) of commercially available (Aldrich, 99% ee) (1R)-(-)-2-azabicyclo[2.2.1]hept-5-en-3-one. The sense of asymmetric induction observed with epoxide 1 using lithium (S,S)-bis(1-phenyl)ethylamide or RLi/4 parallels that observed with exo-norbornene oxide and in our medium-ring study (Ref. 3).
6. Xu, F.; Tillyer, R. D.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J. Tetrahedron: Asymmetry 1998, 9, 1651-1655.
7. n} is also possible, see: Reich, H. J.; Green, D. P.; Medina, M. A.; Goldenberg, W. S.; Gudmundsson, B. O.; Dykstra, R. R.; Phillips, N. H. J. Am. Chem. Soc. 1998, 120, 7201-7210.
8. 2-symmetric bisoxazolines see: Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1-45.
9. Denmark, S. E.; Nicaise, O. J.-C. Chem. Commun. 1996, 999-1004; Shindo, M.; Koga, K.; Tomioka, K. J. Org. Chem. 1998, 63, 9351-9357.
10. Denmark, S. E.; Nicaise, O. J.-C. Chem. Commun. 1996, 999-1004; Shindo, M.; Koga, K.; Tomioka, K. J. Org. Chem. 1998, 63, 9351-9357.
11. For an excellent review on enantioselective syntheses with lithium reagents/sparteine 4 see: Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2283-2316.
12. Mizuno, M.; Kanai, M.; Tomioka, K. Tetrahedron 1997, 31, 10699-10708; Alexakis, A.; Vrancken, E.; Mangeney, P. Synlett 1998, 1165; Oguni, N.; Miyagi, Y.; Itoh, K. Tetrahedron Lett. 1998, 39, 9023-9026.
13. Mizuno, M.; Kanai, M.; Tomioka, K. Tetrahedron 1997, 31, 10699-10708; Alexakis, A.; Vrancken, E.; Mangeney, P. Synlett 1998, 1165; Oguni, N.; Miyagi, Y.; Itoh, K. Tetrahedron Lett. 1998, 39, 9023-9026.
14. Mizuno, M.; Kanai, M.; Tomioka, K. Tetrahedron 1997, 31, 10699-10708; Alexakis, A.; Vrancken, E.; Mangeney, P. Synlett 1998, 1165; Oguni, N.; Miyagi, Y.; Itoh, K. Tetrahedron Lett. 1998, 39, 9023-9026.
15. Amurrio, D.; Khan, K.; Kundig, E. P. J. Org. Chem. 1996, 61, 2258-2259.