Type 2 intramolecular nitroso diels-alder reaction. Synthesis and structure of bridgehead oxazinolactams

Organic Letters

Volumn 2, Issue 10, 2000, Pages 1473-1475

  Sparks, Steven M ^a   Vargas, Jesse D ^a   Shea, Kenneth J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; LACTAM; NITROSO DERIVATIVE; OXAZINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; SYNTHESIS;

INDICATORS AND REAGENTS; LACTAMS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NITROSO COMPOUNDS; OXAZINES;

EID: 0034682142     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005811m     Document Type: Article

References (17)

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3. (b) Kibayashi, C.; Aoyagi, S. Synlett 1995, 873-879.
4. (c) Streith, J.; Defoin, A. Synthesis 1994, 1107-1117.
5. (d) Boger, D. L.; Weinreb, S. M. Hetereo Diels-Alder Methodology in Organic Synthesis; Pergamon: Oxford, 1987.
6. (e) Weinreb, S. M.; Staib, R. R. Tetrahedron 1982, 38, 3087-3128.
7. Shea, K. J.; Pham, P. Q. Tetrahedron Lett. 1983, 24, 1003.
8. Experimental details of the X-ray crystallography can be found in the Supporting Information.
9. For similar studies of bridgehead olefins, see: (a) Lease, T. G.; Shea, K. J. In Advances in Theoretically Interesting Molecules; Thummel, R. P., Ed.; JAI: Greenwich, CT, 1992; Vol. 2, pp 79-112.
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13. Determined by electron diffraction: Chiang, J. F.; Bauer, S. H. J. Am. Chem. Soc. 1969, 91, 1898-1901.
14. For earlier studies of the regiochemistry of intermolecular acyl nitroso Diels-Alder reactions, see: (a) Aoyagi, S.; Tanaka, R.; Naruse, M.; Kibayashi, C. J. Org. Chem. 1998, 63, 8397.
15. (b) Boger, D. L.; Patel, M. J. Org. Chem. 1984, 49, 4098.
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17. Davies, G.; Russel, A. T.; Sanderson, A. J.; Simpson, S. J. Tetrahedron Lett. 1999, 40, 4391.