Selective photocyclization of glycine in dipeptides

Angewandte Chemie (International Edition in English)

Volumn 35, Issue 21, 1996, Pages 2529-2531

  Wyss, Caroline ^a   Batra, Rohit ^a   Lehmann, Christian ^a   Sauer, Stefan ^a   Giese, Bernd ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

Author keywords

Asymmetric syntheses; Diradicals; Peptidemimetics; Photocyclizations

Indexed keywords

EID: 0030461486     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199625291     Document Type: Article

References (7)

1. P. Wessig, P. Wettstein, B. Giese, M. Neuburger. M. Zehnder, Helv: Chim. Acta 1994, 77, 829. For the synthesis of the L-proline derivative, see B. Giese, S. N. Müller, C. Wyss, H. Steiner, Tetrahedron: Asymmetry 1996, 7, 1261.
2. P. Wessig, P. Wettstein, B. Giese, M. Neuburger. M. Zehnder, Helv: Chim. Acta 1994, 77, 829. For the synthesis of the L-proline derivative, see B. Giese, S. N. Müller, C. Wyss, H. Steiner, Tetrahedron: Asymmetry 1996, 7, 1261.
3. A degassed solution (100-200 mL toluene) was cooled to 20-25 °C, and 100-500 mg of 9, 16, or 18 was added. The solution was irradiated with a 150 W Hg high-pressure lamp (Heraeus TQ 150) for 1.5-2.5 h. The products were separated by chromatography. All new compounds were characterized by spectroscopy and elemental analysis.
4. 13C NMR signals of C-4 and C-5 in the δ-lactam rings in 11b-d are Δδ = 0.3-1.3 ppm up field of those of 12b-d.
5. The regioselectivity of the dipeptide cyclization is 8:1 for 9a and greater than 20:1 for 9b-d (25°C).
6. The calculations were carried out at the PMP2/6-31G*//UHF/3-21G* level of theory: Gaussian 94, Revision B.2: M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, J. A. Pople, Gaussian Inc., Pittsburgh, PA, 1995. A similar explanation was used to discuss the preferred hydrogen abstraction from glycine in intermolecular reactions with peptides: C. J. Easton, in Advances in Detailed Reaction Mechanism, Vol. 1, (Ed.: J. M. Coxon), Jai, Greenwich 1991, p. 83.
7. The calculations were carried out at the PMP2/6-31G*//UHF/3-21G* level of theory: Gaussian 94, Revision B.2: M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, J. A. Pople, Gaussian Inc., Pittsburgh, PA, 1995. A similar explanation was used to discuss the preferred hydrogen abstraction from glycine in intermolecular reactions with peptides: C. J. Easton, in Advances in Detailed Reaction Mechanism, Vol. 1, (Ed.: J. M. Coxon), Jai, Greenwich 1991, p. 83.