Table 2.

Iridium-tol-BINAP-catalyzed reductive coupling of oxetanone 1a or azetidinone 1b with racemic allylic acetates 2a-2v to form enantiomerically enriched oxetanols 3a-3v and azetidinols 4a-4v, respectively.^a

^aYields of material isolated by silica gel chromatography. Enantioselectivities were determined by chiral stationary phase HPLC analysis. Standard conditions: 0.2 mmol scale, 18 h for 1a, 36 h for 1b. See Supporting Information for further experimental details.

^b24 h

^c48 h

^d(S)-Ir-tol BINAP (7.5 mol %),

^e(S)-Ir-SEGPHOS (5.0 mol%).

^fDerivatized for ee% determination.