3-Isopropyl-2-cyclopenten-1-one → (s)-3-Isopropylcyclopentanone

Participants

Reaction Steps

General procedure B using (S)-p-tol-BINAP and 3-isopropylcyclopentenone (0.11 g, 0.9 mmol) gave, after 3 d at 0° C. and Kugelrohr distillation (0.4 torr, 220° C.) followed by flash chromatography (10:1 pentane:diethyl ether), the title compound as a clear liquid (0.10 g, 89% yield). In addition to the desired product, starting material (0.011 g, 10%) was also isolated. Spectroscopic data for the title compound were consistent with previously reported data.16 [α]D25° C.−200° (c 1.6, CHCl3) (lit.16 [α]D25° C.−110° (c 1.0, CHCl3) for 60% ee). Chiral GC analysis (Chiraldex G-TA column) indicated that the title compound was obtained in 95% ee.

Provenance & Evidence