Enantiospecific photochemical Norrish/Yang type II reaction of nonbiaryl atropchiral α-oxoamides in solution-axial to point chirality transfer

Journal of the American Chemical Society

Volumn 131, Issue 32, 2009, Pages 11314-11315

  Ayitou, Anoklase Jean Luc ^a   Jesuraj, Josepha L ^a   Barooah, Nilotpal ^a   Ugrinov, Angel ^a   Sivaguru, J ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ATROPISOMERS; CHEMICAL EQUATIONS; CHIRALITY TRANSFER; ENANTIOSPECIFIC; HIGH ENANTIOSELECTIVITY; HYDROGEN ABSTRACTION; OXOAMIDES; PHENYL MOIETIES; REACTION TEMPERATURE; TYPE II;

AMIDES; CHEMICAL REACTIONS; ELECTRON TRANSITIONS; HYDROGEN; STEREOCHEMISTRY;

ENANTIOSELECTIVITY;

ALPHA OXOAMIDE; AMIDE; BETA LACTAM; HYDROGEN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; ISOMER; PHOTOCHEMISTRY; SUBSTITUTION REACTION; TEMPERATURE;

EID: 68849103572     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9050586     Document Type: Article

References (18)

1. (a) Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932-7934.
2. (b) Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155-3212.
3. (a) Inoue, Y. In Chiral Photochemistry; Inoue, Y., Ramamurthy, V., Eds.; Marcel Dekker: New York, 2004; Vol. 11, pp 129-177.
4. (b) Muller, C.; Bach, T. Aust. J. Chem. 2008, 61, 557-564.
5. (c) Hammond, G. S.; Cole, R. S. J. Am. Chem. Soc. 1965, 87, 3256-3257.
6. Sivaguru, J.; Natarajan, A.; Kaanumalle, L. S.; Shailaja, J.; Uppili, S.; Joy, A.; Ramamurthy, V. Acc. Chem. Res. 2003, 36, 509-521.
7. Ayitou, A. J.-L.; Sivaguru, J. J. Am. Chem. Soc. 2009, 131, 5036-5037.
8. (a) Aoyama, H.; Sakamoto, M.; Kuwabara, K.; Yoshida, K.; Omote, Y. J. Am. Chem. Soc. 1983, 105, 1958-1964.
9. (b) Wagner, P. J.; Park, B.-S. Org. Photochem. 1991, 11, 227-366.
10. (c) Chesta, C. A.; Whitten, D. G. J. Am. Chem. Soc. 1992, 114, 2188-2197.
11. (d) Wang, R.; Chen, C.; Duesler, E.; Mariano, P. S. J. Org. Chem. 2004, 69, 1215-1220.
12. (e) Natarajan, A.; Mague, J. T.; Ramamurthy, V. J. Am. Chem. Soc. 2005, 127, 3568-3576.
13. Curran, D. P.; Hale, G. R.; Geib, S. J.; Balog, A.; Cass, Q. B.; Degani, A. L. G.; Hernandes, M. Z.; Freitas, L. C. G Tetrahedron: Asymmetry 1997, 8, 3955-3975.
14. (a) Clayden, J. Chem. Commun. 2004, 127-135.
15. (b) Honda, A.; Waltz, K. M.; Carroll, P. J.; Walsh, P. J. Chirality 2003, 15, 615-621.
16. Refer to Supporting Information.
17. Kitagawa, O.; Fujita, M.; Kohriyama, M.; Hasegawa, H.; Taguchi, T. Tetrahedron Lett. 2000, 41, 8539-8544.
18. Gudmundsdottir, A. D.; Lewis, T. J.; Randall, L. H.; Scheffer, J. R.; Rettig, S. J.; Trotter, J.; Wu, C.-H. J. Am. Chem. Soc. 1996, 118, 6167-6184.