Stereocontrol of Paterno-Buchi photocycloadditions

Tetrahedron Letters

Volumn 38, Issue 31, 1997, Pages 5407-5410

  Fleming, Steven A ^a   Gao, J Jerry ^a  

^a Brigham Young University   (United States)

Author keywords

Oxetane synthesis; Siloxane photochemistry; Stereoselective photocycloaddition

Indexed keywords

BENZALDEHYDE; OXETANE DERIVATIVE; STYRENE;

ARTICLE; CHEMICAL REACTION; CIS TRANS ISOMERISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOCHEMISTRY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030792957     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01201-X     Document Type: Article

References (18)

1. a) Fleming, S. A.; Ward, S. C.; Tetrahedron Lett. 1992, 33, 1013-1016;
2. b) Warf, S. C.; Fleming, S. A.; J. Org. Chem. 1994, 59, 6476-6479;
3. c) Bradford, C. L.; Fleming, S. A.; Ward, S. C.; Tetrahedron Lett. 1995, 36, 4189-4192.
4. Hutchinson, J. H.; Daynard, T. S.; Gillard, J. W. Tetrahedron Lett. 1991, 32, 573.
5. Shea, K. J.; Staab, A. J.; Zandi, K. S. Tetrahedron Lett. 1991, 32, 2715.
6. For a thorough discussion of the mechanism and regioselectivity of the Paterno-Büchi reaction see: Gilbert, A.; Baggott, J. "Essentials of Molecular Photochemistry" Blackwell, 1991, Chapter 7.6, pp 340-353.
7. Our preferred explanation of the stereoselectivity observed in our silyl tethered work (see Ref. 1) is based on the requirement of two π stabilizing groups attached to the styryl moiety and their consistent cis relationship in the 4-membered ring that is formed.
8. Carless, H. A. J.; Maitra, A. K.; Trivedi, H. S. J. Chem. Soc., Chem. Commun. 1979, 984.
9. High pressure liquid chromatography was performed using a Microsorb Si-80-199-C5 silica column eluted with 5% EtOAc in hexane at a flow rate of 3 mL/min.
10. 15O CI m/z calc. 211.1123, obs. 211.1118.
11. Other phenyl substituted oxetanes have exhibited similar trends. See: a) Beereboom, J. J.; von Wittenau, M. S. J. Org. Chem. 1965, 30, 1231;
12. b) Turro, N. J.; Wriede, P. A. J. Am. Chem. Soc. 1968, 90, 6863;
13. c) Yang, N. C.; Eisenhardt, W. J. Am. Chem. Soc. 1971, 93, 1277;
14. d) Yang, N. C.; Kimura, M.; Eisenhardt, W. J. Am. Chem. Soc. 1973, 95, 5058.
15. 15O CI m/z calc. 211.1123, obs. 211.1131.
16. 3) δ 7.2-7.5 (m, 10 H), 6.29 (d, J = 7.8 Hz, 1 H), 5.47 (dq, J = 6.3, 6.3 Hz , 1 H), 4.45 (t, J = 7.8 Hz, 1 H), 1.17 (d, J = 6.3 Hz, 3 H).
17. For an example see: Gottschalk, P.; Neckers, D. C. J. Org. Chem. 1985, 50, 3498.
18. 2Si CI m/z calc. 313.1624, obs. 313.1613.