Table 2.
Asymmetric alkylation of indole 5 with E-vinyldiazoacetate 1b
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entry | catalyst | ratioa of 6/11/12 | yieldb of 6 (%) | ee of 6 (%) |
1 | Rh2(OAc)4 | 62/33/5 | 57 | --- |
2 | Rh2(TFA)4 | 49/44/7 | 43 | --- |
3 | Rh2(esp)2 | 74/26/0 | 52 | --- |
4 | Rh2(S-PTAD)4 | 76/16/8 | 55 | −8 |
5 | Rh2(S-DOSP)4 | 26/38/36 | 22 | 17 |
6 | Rh2(S-TISP)4 | 89/6/5 | 66 | 39 |
7 | Rh2(S-biTISP)2 | 88/9/3 | 66 | 89 |
ratio was the average of two runs and determined from the 1H NMR of the crude reaction mixture.
isolated yield