Stereoselectivity in the Paternò-Büchi reaction of 2,2-diisopropyl-1,3-dioxol with methyl trimethylpyruvate

Tetrahedron Letters

Volumn 37, Issue 8, 1996, Pages 1195-1196

  Buhr, Stefan ^a   Griesbeck, Axel G ^a   Lex, Johann ^a   Mattay, Jochen ^b   Schröer, Jochen ^b  

^a UNIVERSITY OF COLOGNE   (Germany)

^b UNIVERSITY OF KIEL   (Germany)

Author keywords

Endo selectivity; Photocycloaddition; Semiempirical calculations; X ray structure analysis

Indexed keywords

OXETANE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; PHOTOCHEMISTRY; REACTION ANALYSIS; STEREOCHEMISTRY; THERMODYNAMICS; X RAY ANALYSIS;

EID: 0030043288     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02415-8     Document Type: Article

References (19)

1. Electronic Control of Stereoselectivity in Photocycloaddition Reactions: Part 7. Part 6: ref. 3a.
2. a) Griesbeck, A. G. in Handbook of Photochemistry and Photobiology; Horspool, W. A., Song, P.-S., Eds.; CRC Press: Boca Raton, 1995, 550.
3. b) Porco, J. A., Jr., Schreiber, S. L. in Comprehensive Organic Synthesis, Trost, B. M., Fleming, I., Paquette, L. A.., Eds.; Plenum: New York, 1991, 5, 151.
4. c) Carless, H. A. J. in Synthetic Organic Photochemistry, Horspool, W. M., Ed.; Plenum: New York, 1984, 425.
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9. For an excellent discussion of SOC-effects see: Michl, J., Klessinger, M. Excited States and Photochemistry of Organic Molecules, VCH: New York, 1995, 219.
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11. b) Mattay, J., Buchkremer, K., Heterocycles 1988, 27, 2153.
12. -3 Goof = 1.098. Characteristic bond lengths and bond angles: C(4)-O(5) 1.474(11), O(5)-C(6) 1.471(12), C(6)-C(14) 1.557(13), C(4)-C(14) 1.538(12); O(5)-C(4)-C(14) 89.6(8), C(6)-O(5)-C(4) 91.2(8), O(5)-C(6)-C(14) 89.0(9); O(5)-C(6)-C(14)-C(4) 15.6(9). Further details of the crystal structure investigation may be obtained from the Director of the Cambridge Crystallographic Data Centre, 12 Union Road, GB-Cambridge CB21EZ (UK), on quoting the full journal citation.
13. Dewar, M. J. S., Zoebisch, E. G., Healy, E. F., Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
14. 9.
15. Stadtmüller, S., Dissertation: University Würzburg, 1992.
16. The influence of spin-orbit coupling on product stereochemistry has also been studied on a high computational level for the Type A rearrangement of cyclohexenones [a) Zimmerman, H. E., Kutateladze, A. G. J. Org. Chem. 1995,60, 6008.
17. b) Su, M.-D. J. Org. Chem. 1995, 60, 6621] and qualitatively for the inter-and intramolecular enone + ene photocycloaddition
18. [c. Griesbeck, A. G., Stadtmüller, S., Bringmann, G., Busse, H., Buddrus, J. Chem. Ber. 1992, 125, 933-940.
19. d) Becker, D., Klimovich, N. Tetrahedron Lett. 1994, 35, 261].