Asymmetric radical additions of trialkylboranes to 2H-azirine-3- carboxylates

Chemical Communications

Volumn , Issue 18, 2004, Pages 2088-2089

  Risberg, Erik ^a   Fischer, Andreas ^a   Somfai, Peter ^a  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

2H AZIRINE 3 CARBOXYLATE DERIVATIVE; 8 PHENYLMENTHOL; ALKYL GROUP; AZIRIDINE DERIVATIVE; AZIRINE DERIVATIVE; BORANE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; PHENYL GROUP; RADICAL; UNCLASSIFIED DRUG;

ADDITION REACTION; ALKYLATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; DIELS ALDER REACTION; ENANTIOMER; ENANTIOSELECTIVITY; LOW TEMPERATURE; REACTION ANALYSIS; REPRODUCIBILITY; STEREOCHEMISTRY; SYNTHESIS; TECHNIQUE; X RAY CRYSTALLOGRAPHY;

EID: 6344256507     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b408532a     Document Type: Article

References (21)

1. (a) B. Zwanenburg and P. ten Holte, Top. Curr. Chem., 2001, 216, 93;
2. (b) F. Palacios, A. M. Ochoa de Retana, E. Martinez de Marigorta and J. M. de los Santos, Org. Prep. Proced. Int., 2002, 34, 219;
3. (c) T. L. Gilchrist, Aldrichimica Acta, 2001, 34, 51.
4. W. H. Pearson and B. W. Lian, in Comprehensive Heterocyclic Chemistry II, eds. A. R. Katritzky, C. W. Rees and E. F. V. Scriven, Pergamon, Oxford, 1996, Vol. 1a, p. 1.
5. (a) W. McCoull and F. A. Davis, Synthesis, 2000, 1347;
6. (b) D. Tanner, Angew. Chem., Int. Ed. Engl., 1994, 33, 599.
7. E. Risberg and P. Somfai, Tetrahedron: Asymmetry, 2002, 13, 1957.
8. M. J. Alves, G. Fortes, E. Guimarães and A. Lemos, Synlett, 2003, 1403.
9. (a) Å. Sjöholm Timén, A. Fischer and P. Somfai, Chem. Commun., 2003, 1150;
10. (b) Å. Sjôholm Timén and P. Somfai, J. Org. Chem., 2003, 68, 9958.
11. Electrophilic radicals are not compatible with reagents and substrates applied in these reactions. See reference; D. P. Curran, in Comprehensive Organic Synthesis, eds. B. M. Trost and I. Fleming. Pergamon Press, Oxford, 1991, Vol. 4, p. 715.
12. (a) H. Miyabe, C. Ushiro, M. Ueda, K. Yamakawa and T. Naito, J. Org. Chem, 2000, 65, 176;
13. (b) P. Renaud and M. Gerster, Angew. Chem., Int. Ed Engl., 1998, 37, 2562.
14. N. Hailand and K. A. Jørgensen, J. Chem. Soc., Perkin Trans, 1, 2001, 1290.
15. 6.
16. A. Suzuki, A. Arase, H. Matsumoto, M. Itoh, H. C. Brown, M. M. Rogic and M. W. Rathke, J. Am. Chem. Soc., 1967, 89, 5708.
17. (a) A. V. Topchiev, A. A. Prokhorova, Y. M. Paushkin and M. V. Kurashev, Izv. Akad Nauk SSSR, Ser. Khim., 1958, 370;
18. (b) H. C. Brown and U. S. Racherla, J. Org. Chem., 1986, 51, 427;
19. (c) G. W. Kabalka, J. T. Maddox, E. Bogas and S. W. Kelley, J. Org. Chem., 1997, 62, 3688.
20. (a) G. Cardillo, L. Gentilucci and A. Tolomelli, Aldrichimica Acta, 2003, 36, 39;
21. (b) W. K. Lee and H.-J. Ha, Aldrichimica Acta, 2003, 30, 57.