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. Author manuscript; available in PMC: 2013 Apr 6.
Published in final edited form as: Org Lett. 2012 Mar 27;14(7):1934–1937. doi: 10.1021/ol300632p

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
a

ratio was the average of two runs and determined from the 1H NMR of the crude reaction mixture.

b

isolated yield