An ionic chiral auxiliary-induced regioselective and enantioselective Yang photocyclization reaction in the crystalline state

Tetrahedron Letters

Volumn 40, Issue 50, 1999, Pages 8729-8732

  Cheung, Eugene ^a   Kang, Ting ^a   Raymond, Jeff R ^a   Scheffer, John R ^a   Trotter, James ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

Asymmetric induction; Ketones; Photochemistry; Yang photocyclization

Indexed keywords

KETONE;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; CYCLIZATION; ENANTIOMER; MOLECULAR DYNAMICS; MOLECULAR MODEL; PHOTOCHEMISTRY; RACEMIC MIXTURE; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0033544817     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01866-3     Document Type: Article

References (21)

1. For reviews on asymmetric induction studies in organic photochemistry, see: (a) Rau, H. Chem. Rev. 1983, 83, 535;
2. (b) Inoue, Y. Chem. Rev. 1992, 92, 471;
3. (c) Everitt, S. R. L.; Inoue, Y. In Molecular and Supramolecular Photochemistry; Ramamurthy, V.; Schanze, K., Eds.; Marcel Dekker: New York, 1999; Vol. 3, p. 71.
4. While achiral compounds occasionally and unpredictably crystallize in chiral space groups, compounds containing resolved stereogenic centers are required to do so. For reviews dealing with the solid state photochemistry of such systems, see: (a) Vaida, M.; Popovitz-Biro, R.; Leiserowitz, L.; Lahav, M. In Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH Publishers: New York, 1991; Chapter 6;
5. (b) Scheffer, J. R.; Garcia-Garibay, M. In Photochemistry on Solid Surfaces; Anpo, M.; Matsuura, T., Eds.; Elsevier: New York, 1989; Chapter 9.3.
6. (a) Cheung, E.; Netherton, M. R.; Scheffer, J. R.; Trotter, J. J. Am. Chem. Soc. 1999, 121, 2919;
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9. Cyclobutanol products in type II photochemistry were first reported by: Yang, N. C.; Yang, D. H. J. Am. Chem. Soc. 1958, 80, 2913. For a general review of the Norrish/Yang type II reaction, see: Wagner, P.; Park, B.-S. In Organic Photochemistry;Padwa, A., Ed.; Marcel Dekker: New York, 1991; Vol. 11, Chapter 4.
10. Cyclobutanol products in type II photochemistry were first reported by: Yang, N. C.; Yang, D. H. J. Am. Chem. Soc. 1958, 80, 2913. For a general review of the Norrish/Yang type II reaction, see: Wagner, P.; Park, B.-S. In Organic Photochemistry; Padwa, A., Ed.; Marcel Dekker: New York, 1991; Vol. 11, Chapter 4.
11. Ketone a was synthesized by standard methods from the known cis-9-decalylcarboxylic acid (Koch, H.; Haaf, W. Angew. Chem. 1958, 10, 311). All new compounds described in the present paper gave spectroscopic data and elemental analyses completely in accord with their assigned structures. Details will be provided in a subsequent full paper.
12. Cheung, E.; Trotter, J., unpublished results.
13. MM3* and MM+ (HyperChem) gave essentially identical results.
14. For a discussion of the geometric requirements for γ-hydrogen atom abstraction in the Norrish type II reaction, see: Ihmels, H.; Scheffer, J. R. Tetrahedron 1999, 55, 885.
15. For an analogous photoreaction involving cyclization to a six-membered ring ketone, see: Perkins, M. J.; Peynircioglu, N. B.; Smith, B. V. J. Chem. Soc., Chem. Commun. 1976, 222.
16. In general, β-hydrogen abstraction in the photochemistry of ketones is very rare. For examples, see: (a) Henning, H.-G. In The CRC Handbook of Organic Photochemistry and Photobiology; Horspool, W. M.; Song, P.-S., Eds.; CRC Press: Boca Raton, 1995; Chapter 40;
17. (b) Scheffer, J. R.; Dzakpasu, A. A. J. Am. Chem. Soc. 1978, 100, 2163;
18. (c) Couture, A.; Hoshino, M.; De Mayo, P. J. Chem. Soc., Chem. Commun. 1976, 131.
19. For an analogous situation in a different system, see: (a) Jones, R.; Scheffer, J. R.; Trotter, J.; Yang, J. Tetrahedron Lett. 1992, 33, 5481;
20. (b) Jones, R.; Scheffer, J. R.; Trotter, J.; Yang, J. Acta Crystallogr. 1994, B50, 601.
21. Re face defined with respect to conformer A in Fig. 1.