Table 1.

Selected Enantioselective Indole Functionalization Optimization Experiments^a

entry	solvent	catalyst	yield(%)b	ee(%)c
1	PhMe	Rh2(S-PTTL)4	73	85
2	PhMe	Rh2(S-TCPTTL)4	20	76
3	PhMe	Rh2(S-NTTL)4	95	95
4	PhMe	Rh2(R-PTAD)4	54	–91
5	PhMe	Rh2(S-DOSP)4	24	20
6	CH2Cl2	Rh2(S-NTTL)4	56	92
7d	PhMe	Rh2(S-NTTL)4	36	85

^aConditions: indole (0.2 M), Rh-cat (0.5 mol %) at –78 °C, α-diazoester (0.67 M) added via syringe pump.

^bIsolated yield.

^cDetermined by chiral HPLC analysis.

^dReaction run at 0 °C. Optimal conditions in bold.