Parallel kinetic resolution of 4-alkynals catalyzed by Rh(I)/Tol-BINAP: synthesis of enantioenriched cyclobutanones and cyclopentenones

J Am Chem Soc. 2003 Jul 9;125(27):8078-9. doi: 10.1021/ja035489l.

Abstract

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.