Asymmetric synthesis via heterocyclic intermediates. I. Synthesis of 3,4-dihydro-11a-(S)-methyl-4-(R)-phenyl-1,4-oxazino[4,3-b]isoquinolin-1(6H,11H)-one

José L. Marco

Instituto de Química Orgánica General, CSIC, 3, Juan de la Cierva, 28006-Madrid, Spain

José L. Marco

Instituto de Química Orgánica General, CSIC, 3, Juan de la Cierva, 28006-Madrid, Spain

First published: July/August 1987

Citations: 8

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The synthesis of 3,4-dihydro-11a-(S)-methyl-4-(R)-phenyl-1,4-oxazino[4,3-b]isoquinoline-1(6H,11H)-one 1 is described.

References and Notes

1a R. Cahill and T. A. Crabb, Org. Magn. Reson., 4, 283, 509 (1972);
10.1002/mrc.1270040209
CAS Web of Science® Google Scholar
b S. S. Jew, S. Terashima and K. Koga, Tetrahedron, 35, 2345 (1979);
10.1016/S0040-4020(01)93748-2
CAS Web of Science® Google Scholar
c G. Coppola, J. Heterocyclic Chem., 18, 767 (1981);
10.1002/jhet.5570180427
CAS Web of Science® Google Scholar
d X. Yan and Z. Weng, Yaoxue Xuebao, 20, 312 (1985);
CAS PubMed Google Scholar
Chem. Abstr., 103, 104903h (1986).
Google Scholar
2a J. L. Marco, J. Royer and H.-P. Husson, Tetrahedron Letters, 3567 (1985)
Google Scholar
b J. L. Marco, J. Royer and H.-P. Husson, Tetrahedron Letters, 6345 (1985).
Google Scholar
3 K. Weinges, K. Gries, B. Stemmle and W. Schrank, Chem. Ber., 110, 2098 (1977).
10.1002/cber.19771100607
CAS Web of Science® Google Scholar
4 The absolute configuration of 1 has not been independently established. It is assumed to have the same absolute configuration in C-11a as the major epimer in 3, whose absolute configuration had been previously assigned by ¹H-nmr analysis [2a].
Google Scholar
5 W. M. Whaly and T. R. Govindachari, Org. React., 6, 151 (1951).
Google Scholar
6 H. Singh and R. Sarin, Heterocycles, 23, 107 (1985).
10.3987/R-1985-01-0107
CAS Web of Science® Google Scholar
7 H. C. Hiemstra, H. Bierangel, M. Wijnberg and U. K. Pandit, Tetrahedron, 39, 3981 (1984) and references cited therein.
10.1016/S0040-4020(01)90904-4
CAS Web of Science® Google Scholar

July/August 1987

Pages 1235-1236