New Route to Synthesize Enantiopure 6-Methyl and 6-Ethyl Bicyclic Lactams Derived from (R)-(-)-2-Phenylglycinol
Keywords:
Enantiopure bicyclic lactamsAbstract
Abstract. The diastereoselective synthesis of bicyclic lactams (-)-(3R,6S,8aS)-6-methyl- and -6-ethyl-3-phenyl-hexahydrooxazolo[3,2-a]pyridin-5-ones 4(a-b) and (-)-(3R,6R,8aS)-6-methyl-3-phenyl-hexahydrooxazolo[3,2-a]pyridin-5-one 4’a are described.
Resumen. Se describe la síntesis diasteroselectiva de las biciclo lactamas (-)-(3R,6S,8aS)-6-metil- y -6-etil-3-fenil-hexahidrooxazol[3,2-a]piridin-5-onas 4(a-b), y la (-)-(3R,6R,8aS)-6-metil-3-fenil-hexahidrooxazol[3,2-a]piridin-5-ona 4’a.
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References
1. a) Amat, M.; Escolano, C.; Lozano, O.; Gómez-Esqué, A.; Griera, R.; Molins, E.; Bosch, J. J. Org. Chem. 2006, 71, 3804-3815. b) Amat, M.; Llor, N.; Hidalgo, J.; Bosch, J. Tetrahedron-Asymmetry 1997, 8, 2237-2240. c) Amat, M.; Llor, N.; Hidalgo, J.; Hernández, A.; Bosch, J. Tetrahedron-Asymmetr. 1996, 7, 977-980. d) Amat, M.; Pshenichnyi, G.; Bosch, J.; Molis, E.; Miravitlles, C. Tetrahedron-Asymmetry 1996, 7, 3091-3094.
2. Gnecco, D.; Marazano, C.; Enríquez, R.; Terán, J. L.; Sánchez, M.; Galindo, A. Tetrahedron-Asymmetry 1998, 9, 2027-2029.
3. Mabic, S.; Castagnoli, Jr., N. J. Org. Chem. 1996, 61, 309-313.
4. The so different diastereomeric ratios observed for epimeric mixtures 2a (60:40) and 2b (90:10) could be associated the size of the substituent at C-3.
5. Terán, J. L.; Gnecco, D.; Galindo, A.; Juárez, J.; Bernès, S.; Enríquez, R. Tetrahedron-Asymmetry 2001, 12, 357-360.
6. Amat, M.; Escolano, C.; Núria, L.; Lozano, O.; Gómez-Esqué, A.; Griera, R.; Bosch, J. Arkivoc 2005, ix, 115-123.
7. Crystallographic data of 4’a have been deposited with the Cambridge Crystallographic Data Centre CCDC 618864. Copies of the data can be obtained, free charge, on application to CCDC,
12 Union Road, Cambridge CB2 1EZ, UK e-mail: deposit@ccdc.cam.ac.uk
2. Gnecco, D.; Marazano, C.; Enríquez, R.; Terán, J. L.; Sánchez, M.; Galindo, A. Tetrahedron-Asymmetry 1998, 9, 2027-2029.
3. Mabic, S.; Castagnoli, Jr., N. J. Org. Chem. 1996, 61, 309-313.
4. The so different diastereomeric ratios observed for epimeric mixtures 2a (60:40) and 2b (90:10) could be associated the size of the substituent at C-3.
5. Terán, J. L.; Gnecco, D.; Galindo, A.; Juárez, J.; Bernès, S.; Enríquez, R. Tetrahedron-Asymmetry 2001, 12, 357-360.
6. Amat, M.; Escolano, C.; Núria, L.; Lozano, O.; Gómez-Esqué, A.; Griera, R.; Bosch, J. Arkivoc 2005, ix, 115-123.
7. Crystallographic data of 4’a have been deposited with the Cambridge Crystallographic Data Centre CCDC 618864. Copies of the data can be obtained, free charge, on application to CCDC,
12 Union Road, Cambridge CB2 1EZ, UK e-mail: deposit@ccdc.cam.ac.uk
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2020-08-05
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