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. Author manuscript; available in PMC: 2010 Aug 6.
Published in final edited form as: J Am Chem Soc. 2008 Feb 27;130(11):3262–3263. doi: 10.1021/ja710065h

Table 2.

Carbodiimide Scope

graphic file with name nihms214576u4.jpg
entry R 3:4b yield (%) of 3c ee (%) of 3d
1 p-OMe, 2b 3.6: 1 70 94
2 o-OMe, 2c 3.8: 1 68 (62)e 98 (96)e
3 m-Cl, 2d 3.4: 1 67 97
4 o-CF3, 2e 9.4: 1 82 97
5f p-CN, 2f 9.5: 1 55 92
a

Conditions: 1 (2 equiv), 2 (0.16 mmol), Rh catalyst, L in PhMe at 110 °C.

b

Product selectivity (3: 4) is determined by 1H NMR of the unpurified reaction mixture.

c

Isolated yield.

d

Determined by HPLC analysis using a chiral stationary phase.

e

0.8 mmol scale of 2c, 1 mol% Rh catalyst and 2 mol% L4.

f

5 mol % Rh catalyst and 10 mol % L4.