Palladium-catalyzed, one-pot, three-component synthesis of homoallylic amines from aldehydes, anisidine, and allyl trifluoroacetate

Organic Letters

Volumn 11, Issue 2, 2009, Pages 485-488

  Grote, Robin E ^a   Jarvo, Elizabeth R ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 62149088819     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8026297     Document Type: Article

References (32)

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11. For palladium-catalyzed formation of allylic boronates, see: (b) Ishiyama, T.; Ahiko, T.; Miyaura, N. Tetrahedron Lett. 1996, 37, 6889-6892.
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14. In related studies, enantioselective catalysis of reactions of allenes affords a chiral allylic boronate that undergoes a stereospecific type I allylation reaction with aldehydes and imines: (a) Sieber, J. D.; Morken, J. P. J. Am. Chem. Soc. 2006, 128, 74-75.
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18. Manuscript in preparation.
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24. See Supporting Information for details.
25. NHC-ligated palladium complexes such as the one shown in Scheme 1b did not catalyze allylsilane formation under these reaction conditions. In related studies ligation of two monodentate ligands was shown to inhibit allylsilane formation. See: Macsára, I.; Hupe, E.; Szabó, K. J. Org. Chem. 1999, 64, 9547-9556.
26. The source of the water was inferred to be the commercially available TBAF. The use of drying agents did not decrease the formation of homoallylic alcohol. See Supporting Information for details.
27. This hypothesis was based primarily on our preliminary studies of palladium-catalyzed imine allylation using allylstannanes. Grote, R. E.; Jarvo, E. R. Unpublished results. See also ref 4a.
28. This chemoselectivity may be due to increased ability of imine to coordinate to the palladium catalyst. For a discussion, see: Denmark, S. E.; Almstead, N. G. J. Am. Chem. Soc. 1993, 115, 3133-3139.
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32. 1H NMR <5% of benzaldehyde was in solution after 22 h.