Direct, intermodular, enantioselective, iridium-catalyzed allylation of carbamates to form carbamate-protected, branched allylic amines

Organic Letters

Volumn 11, Issue 13, 2009, Pages 2944-2947

  Weix, Daniel J ^a   Markovič, Dean ^a   Ueda, Mitsuhiro ^a   Hartwig, John F ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; AMINE; CARBAMIC ACID DERIVATIVE; CARBONIC ACID DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; IRIDIUM; ORGANOMETALLIC COMPOUND; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALLYL COMPOUNDS; AMINES; CARBAMATES; CARBONATES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; INDICATORS AND REAGENTS; IRIDIUM; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; STEREOISOMERISM;

EID: 67649499974     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901151u     Document Type: Article

References (22)

1. Johannsen, M.; Jorgensen, K. A. Chem. Rev. 1998, 98, 1689-1708.
2. For an alternate disconnection see: Lee, A.; Ellman, J. A. Org. Lett. 2001, 3, 3707-3709.
3. Connell, R. D.; Rein, T.; Åakermark, B.; Helquist, P. J. Org. Chem. 1988, 53, 3845-3849.
4. Singh, O. V.; Han, H. Tetrahedron Lett. 2007, 48, 7094-7098.
5. Inoue, Y.; Taguchi, M.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1985, 58, 2721-2722.
6. Weihofen, R.; Tverskoy, O.; Heimchen, G. Angew. Chem., Int. Ed. 2006, 45, 5546-5549.
7. Pouy, M. J.; Leitner, A.; Weix, D. J.; Ueno, S.; Hartwig, J. F. Org. Lett. 2007, 9, 3949-3952.
8. Singh, O. V.; Han, H. J. Am. Chem. Soc. 2007, 129, 774-775.
9. Overman, L. E.; Carpenter, N. E. Org. React. (N.Y.) 2005, 66, 1107.
10. 3H as the nucleophile source see: Defieber, C.; Anger, M. A.; Moriel, P.; Carreira, E. M. Angew. Chem., Int. Ed. 2007, 46, 31393143.
11. Leitner, A.; Shu, C.; Hartwig, J. F. Org. Lett. 2005, 7, 1093-1096.
12. Many bases were tested, and only reactions conducted with K3P04, Cs2C03 and CsF resulted in high yields of the desired product. See Supporting Information for details.
13. Feringa, B. L. Acc. Chem. Res. 2000, 33, 346-353.
14. Alexakis, A.; Polet, D. Org. Lett. 2004, 6, 3529-3532.
15. Leitner, A.; Shekhar, S.; Pouy, M. J.; Hartwig, J. F. J. F. J. Am. Chem. Soc. 2005, 127, 15506-15514.
16. Stanley, L. M.; Hartwig, J. F. J. Am. Chem. Soc. 2009, 131, ASAP, DOI: 10.1021/ia902243s.
17. Ueno, S.; Hartwig, J. F. Angew. Chem., Int. Ed. 2008, 47, 19281931.
18. Basel, Y.; Hassner, A. Synthesis 2001, 550-552.
19. Houlihan, F.; Bouchard, F.; Fréchet, J. M. J.; Willson, C. G. Can. J. Chem. 1985, 63, 153-162.
20. Singh, O. V.; Han, H. Org. Lett. 2007, .9, 4801-4804.
21. Trost, B. M.; Van Vranken, D. L. Angew. Chem., Int. Ed. Engl. 1992, 31, 228-230. See Supporting Informationfor the structures.
22. Initial attempts to conduct enantioselective Pd-catalyzed carbamate allylation reactions have been unsuccessful.