Parallel kinetic resolution of 4-alkynals catalyzed by Rh(I)/Tol-BINAP: synthesis of enantioenriched cyclobutanones and cyclopentenones.
A Rh(I)/(R)-Tol-BINAP catalyst reacts with a racemic mixture of 4-alkynals to selectively furnish a cyclobutanone from the (R)-substrate and a cyclopentenone from the (S)-substrate. This method is noteworthy from several standpoints, including the scarcity of parallel kinetic resolutions (especially those that are catalyzed or that involve carbon-carbon bond formation) and the dearth of catalytic processes that generate enantioenriched cyclobutanones.
Tanaka
Ken
K
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA.
Fu
Gregory C
GC