Highly enantioselective Rh-catalyzed carboacylation of olefins: efficient syntheses of chiral poly-fused rings.

Autor: Xu T; Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas 78712, United States., Ko HM, Savage NA, Dong G
Jazyk: angličtina
Zdroj: Journal of the American Chemical Society [J Am Chem Soc] 2012 Dec 12; Vol. 134 (49), pp. 20005-8. Date of Electronic Publication: 2012 Nov 28.
DOI: 10.1021/ja309978c
Abstrakt: Here we report the first highly enantioselective Rh-catalyzed carboacylation of olefins via C-C bond activation of benzocyclobutenones. Good yields and excellent enantioselectivities (92-99% ee, 14 examples) were obtained for substrates with various steric and electronic properties. In addition, fully saturated poly-fused rings were prepared from the carboacylation products through a challenging catalytic reductive dearomatization approach. These investigations provide a distinct way to prepare chiral carbon frameworks that are nontrivial to access with conventional methods.
Databáze: MEDLINE