Desymmetrisation of bicyclic, meso-anhydrides by proline esters

Tetrahedron Letters

Volumn 38, Issue 5, 1997, Pages 889-892

  Jones, Iwan G ^a   Jones, Wyn ^b   North, Michael ^a   Teijeira, Marta ^c   Uriarte, Eugenio ^c  

^a BANGOR UNIVERSITY   (United Kingdom)

^b Peboc Div of Eastman Chemical Ltd   (United Kingdom)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; PROLINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; METHODOLOGY; STEREOCHEMISTRY;

EID: 0031016070     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02433-1     Document Type: Article

References (13)

1. North, M.; Zagotto, G.; Synlett, 1995, 639; Albers, T.; Biagini, S.C.G.; Hibbs, D.E.; Hursthouse, M.B.; Malik, K.M.A.; North, M.; Uriarte, E.; Zagotto, G.; Synthesis, 1996, 393.
2. North, M.; Zagotto, G.; Synlett, 1995, 639; Albers, T.; Biagini, S.C.G.; Hibbs, D.E.; Hursthouse, M.B.; Malik, K.M.A.; North, M.; Uriarte, E.; Zagotto, G.; Synthesis, 1996, 393.
3. Jones, I.G.; Jones, W.; North, M.; Synlett, accepted for publication.
4. 13C NMR, IR, m/z, and HRMS).
5. Full details of the X-ray analysis will be published elsewhere.
6. Canone, P.; Akssira, M.; Dahdouh, A.; Kasmi, H.; Boumzebra, M.; Tetrahedron, 1993, 49, 1985; Furuta, K.; Hayashi, S.; Miwa, Y.; Yamamoto, H.; Tetrahedron Lett., 1987, 28, 5841, Arai, Y.; Kawanami, S.; Koizumi, T.; J. Chem. Soc., Perkin Trans. 1, 1991, 2969; Zegaff, C.; Poncet, J.; Jouin, P.; Dufour, M-N.; Castro, B.; Tetrahedron, 1989, 45, 5039.
7. Canone, P.; Akssira, M.; Dahdouh, A.; Kasmi, H.; Boumzebra, M.; Tetrahedron, 1993, 49, 1985; Furuta, K.; Hayashi, S.; Miwa, Y.; Yamamoto, H.; Tetrahedron Lett., 1987, 28, 5841, Arai, Y.; Kawanami, S.; Koizumi, T.; J. Chem. Soc., Perkin Trans. 1, 1991, 2969; Zegaff, C.; Poncet, J.; Jouin, P.; Dufour, M-N.; Castro, B.; Tetrahedron, 1989, 45, 5039.
8. Canone, P.; Akssira, M.; Dahdouh, A.; Kasmi, H.; Boumzebra, M.; Tetrahedron, 1993, 49, 1985; Furuta, K.; Hayashi, S.; Miwa, Y.; Yamamoto, H.; Tetrahedron Lett., 1987, 28, 5841, Arai, Y.; Kawanami, S.; Koizumi, T.; J. Chem. Soc., Perkin Trans. 1, 1991, 2969; Zegaff, C.; Poncet, J.; Jouin, P.; Dufour, M-N.; Castro, B.; Tetrahedron, 1989, 45, 5039.
9. Canone, P.; Akssira, M.; Dahdouh, A.; Kasmi, H.; Boumzebra, M.; Tetrahedron, 1993, 49, 1985; Furuta, K.; Hayashi, S.; Miwa, Y.; Yamamoto, H.; Tetrahedron Lett., 1987, 28, 5841, Arai, Y.; Kawanami, S.; Koizumi, T.; J. Chem. Soc., Perkin Trans. 1, 1991, 2969; Zegaff, C.; Poncet, J.; Jouin, P.; Dufour, M-N.; Castro, B.; Tetrahedron, 1989, 45, 5039.
10. Similar ring opening reaction of cyclopropylamines bearing an electron withdrawing substituent on the cyclopropane ring have previously been reported. Cannon, J.G.; Garst, J.E.; J. Org. Chem., 1975, 40, 182; Augustine, R.L.; Pinto, F.G.; J. Org. Chem., 1975, 40, 115.
11. Similar ring opening reaction of cyclopropylamines bearing an electron withdrawing substituent on the cyclopropane ring have previously been reported. Cannon, J.G.; Garst, J.E.; J. Org. Chem., 1975, 40, 182; Augustine, R.L.; Pinto, F.G.; J. Org. Chem., 1975, 40, 115.
12. Hronowski, L.J.J.; Szarek, W.A.; Can J. Chem., 1988, 66, 61.
13. Bridges, A.J.; Sundara, R.P.; Ng, G.S.Y.; Jones, J.B.; J. Am. Chem. Soc., 1984, 106, 1461.