Rapid decarboxylative allylation of nitroalkanes

Organic Letters

Volumn 12, Issue 4, 2010, Pages 740-742

  Grenning, Alexander J ^a   Tunge, Jon A ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE; ALLYL COMPOUND; AMINE; NITRO DERIVATIVE;

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

ALKANES; ALLYL COMPOUNDS; AMINES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; MOLECULAR STRUCTURE; NITRO COMPOUNDS; STEREOISOMERISM;

EID: 76849085106     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol902828p     Document Type: Article

References (17)

1. For reviews of allylation of aldimines, see: Ding, H.; Friestad, G. K. Synthesis 2005, 2815-3282
2. (b) Shibasaki, M.; Kanai, M. Chem. Rev. 108, 2853, 287.
3. Burger, E., C.; Tunge, J. A. J. Am. Chem. Soc. 2006, 128, 10002-10003.
4. Yeagley, A. A.; Chruma, J. J. Org. Lett. 2007, 9, 2979-12882
5. (a) Shimizu, I.; Yamada, T.; Tsuji, J. Tetrahedron Lett. 1980, 3199.
6. (b) Tsuda, T.; Chujo, Y.; Nishi, S.-i.; Tawara, K.; Saegusa, T. J. Am. Chem. Soc. 1980, 102, 6381.
7. (c) Waetzig, S. R.; Tunge, J. A. J. Am. Chem. Soc. 2007, 129, 14860-14861.
8. (d) Weaver, J. D.; Tunge, J. A. Org. Lett. 2008, 10, 4657-4660.
9. Ono, N. The Nitro Group in Organic Synthesis; Feuer, H., Ed.; Wiley-VCH: New York, 2001; pp 140-147.
10. (a) Aleksandrowicz, P.; Piotrowska, H.; Sas, W. Tetrahedron 1982, 38, 1321-1327.
11. (b) Wade, P. A.; Morrow, S. D.; Hardinger, S. A. J. Org. Chem. 1982, 47, 365-367.
12. Maki, K.; Kanai, M.; Shibasaki, M. Tetrahedron 2007, 63, 4250-4257. Isolated yields were not reported.
13. Tsuji, J.; Yamada, T.; Minami, I.; Yuhara, M.; Nisar, M.; Shimizu, I. J. Org. Chem. 1987, 52, 2989-2995.
14. 3 with the chelating ligand (rac)-BINAP failed to give any conversion under these conditions.
15. Allylation of a-bromo nitroalkanes with allylstannanes: Ono, N.; Zinmeister, K.; Kaji, A. Bull. Chem. Soc. Jpn. 1985, 38, 1069-1070.
16. Wade, P. A.; Murray, J. K., Jr.; Shah-Patel, S.; Carroll, P. J. Tetrahedron Lett. 2002, 43, 2585-2588.
17. See Supporting Information for a table of substrate and product dr's.