Enantioselective rhodium(I)-triethylamine catalyzed addition of potassium isopropenyl trifluoroborate to enones

Tetrahedron Letters

Volumn 49, Issue 33, 2008, Pages 4894-4896

  Lalic, Gojko ^a   Corey, E J ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIC ENONE DERIVATIVE; KETONE DERIVATIVE; POTASSIUM DERIVATIVE; POTASSIUM ISOPROPENYL TRIFLUOROBORATE; RHODIUM COMPLEX; TRIETHYLAMINE;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; COMPLEX FORMATION; ENANTIOSELECTIVITY; REACTION ANALYSIS;

EID: 46049105895     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.05.147     Document Type: Article

References (9)

1. Lalic G., and Corey E.J. Org. Lett. 9 (2007) 4921-4923
2. Krause N., and Hoffmann-Roder A. Synthesis (2001) 171-196
3. Alexakis A., and Benhaim C. Eur. J. Org. Chem. (2002) 3221-3236
4. Hayashi T., and Yamasaki K. Chem. Rev. 103 (2003) 2829-2844
5. Pucheault M., Darses S., and Genêt J.P. Eur. J. Org. Chem. (2002) 3552-3557
6. The beneficial effect of triethylamine on the rate of rhodium catalyzed 1,4-additions to enones has been reported:. Itooka R., Iguchi Y., and Miyaura N. J. Org. Chem. 68 (2003) 6000-6004
7. 4 and filtered. Solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography.
8. The absolute configuration of the products was assigned by analogy to the assignment made for compound 4, which was elaborated into a product of a known absolute stereochemistry (see Ref. 1 for details).
9. Hayashi T., Takahashi M., Takaya Y., and Ogasawara M. J. Am. Chem. Soc. 124 (2002) 5052