Asymmetric allylation, crotylation, and cinnamylation of N-heteroaryl hydrazones

Organic Letters

Volumn 12, Issue 4, 2010, Pages 688-691

  Feske, Miriam Inbar ^a   Santanilla, Alexander Buitrago ^a   Leighton, James L ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 76849089747     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol9026864     Document Type: Article

References (16)

1. For two recent reviews, see: (a) Ding, H.; Friestad, G. K. Synthesis 2005, 2815.
2. (b) Friestad, G. K.; Mathies, A. K. Tetrahedron 2007, 63, 2541.
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9. (b) Sugiura, M.; Bobvieux, F.; Kobayashi, S. Synlett 2003, 1749.
10. We could find no examples of the use of such hydrazones in. nucleophilic addition reactions. There are reports on the use of such hydrazones as ligands in coordination complexes. See, for example: (a) Tupolova, Y. P.; Lukov, V. V.; Kogan, V. A.; Popov, L. D. Russ. J. Coord. Chem. 2007, 33, 301.
11. (b) Tang, J.; Costa, J. S.; Pevec, A.; Kozlevcar, B.; Massera, C.; Roubeau, O.; Mutikainen, I.; Turpeinen, U.; Gamez, P.; Reedijk, J. Cryst. Growth Des. 2008, 8, 1005.
12. (a) Hearn, M. J.; Chung, E. S. Synth. Commun. 1980, 10, 253.
13. (b) Toti, A.; Frediani, P.; Salvini, A.; Rosi, L.; Giolli, C. J. Oreanomet. Chem. 2005, 690, 3641.
14. Preparation of hydrazone 3 and all other hydrazones described herein was straightforward: the commercially available 2-chloroheteroarene is treated with hydrazine, and the resulting N-heteroarylhydraine is condensed with, the aldehyde. See the Supporting Information for details.
15. (a) Burk, M. J.; Martinez, J. P.; Feaster, J. E.; Cosford, N. Tetrahedron 1994, 50, 4399.
16. (b) Ding, H.; Friestad, G. K. Org. Lett. 2004, 6, 637.