Table 1.

Influence of various reaction parameters in the optimization of the enantioselective iridium-catalyzed C-C coupling of CF₃-allene 1i with methanol to form alcohol 2i.^a

Entry	Ir(I)Ln	Additive (mol%)	T °C	Yield (%)	ee (%)
1	[Ir(cod)Cl]2	---	70	56	64
2	Ir(cod)(acac)	---	70	14	79
3	Ir(cod)(acac)	---	80	79	79
4	Ir(cod)(acac)	H2O (500 mol%)	80	56	89
5	Ir(cod)(acac)	TBAI (10 mol%)	80	79	84
6	Ir(cod)(acac)	H2O/TBAI	80	81	90
7b	Ir(cod)(acac)	H2O/TBAI	80	72	94

^aYields of material isolated by silica gel chromatography. Enantioselectivities were determined by chiral stationary phase HPLC analysis.

^bEtOAc solvent.