Stereocontrolled intramolecular nitrile oxide cycloaddition reaction using a gauche-gauche interaction

Tetrahedron Letters

Volumn 48, Issue 20, 2007, Pages 3539-3542

  Noguchi, Michihiko ^a   Tsukimoto, Aiko ^a   Kadowaki, Ayako ^a   Hikata, Jun ^a   Kakehi, Akikazu ^b  

^a YAMAGUCHI UNIVERSITY GRADUATE SCHOOL OF MEDICINE   (Japan)

^b SHINSHU UNIVERSITY   (Japan)

Author keywords

Gauche gauche interaction; Intramolecular nitrile oxide cycloaddition; Stereocontrol

Indexed keywords

ACETALDOXIME; CARBON; NITRILE OXIDE; NITROGEN; PROPIONALDEHYDE;

ARTICLE; CYCLOADDITION; MOLECULAR INTERACTION; OXIDATION; PURIFICATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 34247163627     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.03.094     Document Type: Article

References (22)

1. For recent reviews on nitrone cycloadditions:. Frederickson M. Tetrahedron 53 (1997) 403-425
2. Gothelf K.V., and Jørgensen K.A. Chem. Commun. (2000) 1449-1457
3. Bates R.W., and Sa-Ei K. Tetrahedron 58 (2002) 5878-5978
4. Adams J.P. J. Chem. Soc., Perkin Trans. 1 (2002) 2586-2597
5. For recent reviews on nitrone and nitrile oxide cycloadditions:. Chiacchio U., Rescifina A., and Romeo G. Targets in Heterocyclic Systems 1 (1997) 225-276
6. Loubinoux B., Gerardin P., Schneider R., Ahrach M., and Boelle J. Trends Heterocycl. Chem. 4 (1995) 135-158
7. Namboothin I.N.N., and Hassner A. Top. Curr. Chem. 216 (2001) 1-49
8. Chiacchio U., Corsaro A., Librando V., Rescifina A., and Roberto G. Tetrahedron 52 (1996) 14323-14334
9. Enders D., Haertwig A., and Runsink J. Eur. J. Org. Chem. (1998) 1793-1802
10. Marrugo H., Dogbeavou R., and Breau L. Tetrahedron Lett. 40 (1999) 8979-8983
11. Uddin Md.J., Kikuchi M., Takedatsu K., Arai K.-I., Kakehi A., Irie R., Shirai H., and Yamamoto I. Synthesis (2000) 365-375
12. Ishikawa T., Urano J., Ikeda S., Kobayashi Y., and Saito S. Angew. Chem., Int. Ed. 41 (2002) 1586-1588
13. Scott J.P., Oliver S.F., Brands K.M.J., Brewer S.E., Davies A.J., Gibb A.D., Hands D., Keen S.P., Sheen F.J., Reamer R.A., Wilson R.D., and Dolling U.-H. J. Org. Chem. 71 (2006) 3086-3092
14. Tanaka M., Hikata J., Yamamoto H., and Noguchi M. Heterocycles 55 (2001) 223-226
15. 1,3-strain for this interaction. However, in order to obtain a better understanding for this chemistry, we prefer the term of gauche-gauche interaction correctly.
16. Aldehydes 1 were prepared according to the following scheme:{A figure is presented}
17. 3), 31.0 (7-C), 44.2 (4-C), 46.9 (3a-C), 48.9 (6-C), 70.6 (3-C), 126.9, 130.0, 137.4, 143.8 (Ar-C), 155.1 (7a-C).
18. During the preparation of this manuscript, a communication on the intramolecular nitrile oxide cycloaddition stereocontrolled based on the same as our strategy was found;. Kadowaki A., Nagata Y., Uno H., and Kamimura A. Teterahedron Lett. 48 (2007) 1823-1825
19. Structures of hexahydroisoxazolo[4,3-c]pyridine 4a and hexahydroisoxazolo[3,4-c]pyridine 8d were confirmed by single crystal X-ray structure analysis and their crystallographic data have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 621689 for 4a and CCDC 621692 for 8d. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
20. 11{A figure is presented}
21. 3), 32.3 (4-C), 40.1 (7-C), 44.0(3a-C), 53.1 (5-C), 73.9 (3-C), 127.3, 129.9, 137.2, 143.9 (Ts-C), 157.8 (7a-C).
22. Veenstra S.J., and Schmid P. Tetrahedron Lett. 38 (1997) 997-1000