Table 1. Preliminary investigation of ligands in hydrogenation of cyclic 1,3-diketones ^a .

Entry	Ligand	Conversion b	dr c	ee c
1	f-amphox	24%	7.3/1	93%
2	Indan-f-amphox	11%	5.4/1	28%
3	f-amphol	50%	4.1/1	37%
4	f-ampha	84%	10.1/1	95%

^aReaction conditions: 1a (0.1 mmol, 0.1 M), 1a/[Ir(COD)Cl]₂/ligand/base = 500/0.5/1.1/10, 20 atm H₂, rt, 1 h.

^bConversion was determined by ¹H NMR analysis, no by-product was observed.

^cdr and ee were determined by HPLC on a chiral stationary phase.