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. Author manuscript; available in PMC: 2008 Oct 31.
Published in final edited form as: J Am Chem Soc. 2007 Oct 5;129(43):12948–12949. doi: 10.1021/ja0762240

Table 3.

Scope of Enantioselective Carboamination with (R,R)-11aa

entry substrate product yield (%)b ee (%)c ERc
graphic file with name nihms64159t1.jpg graphic file with name nihms64159t2.jpg
1 1a, R1 = Me, R2 = Me 2a 85 92 96:4
2 1b, R1= Me, R2 = H 2b 73 92 96:4
3 1c, R1= Me, R2 = Cl 2c 45 92 96:4
4 1d, R1= Me, R2 = OMe 2d 75 94 97:3
5 1e, R1= Ph, R2 = Me 2e 78 94 97:3
6 1f, R1 = -CH2(CH2)2CH2-, R2= Me 2f 83 92 96:4
7 1g, R1= -CH2(CH2)3CH2-, R2 = Me 2g 68 92 96:4
8 1h, R1= H, R2 = Me 2h 68 80 90:10
9 1i, R1 = H, R2= H 2i 77 82 91:9
10d graphic file with name nihms64159t3.jpg
14 		graphic file with name nihms64159t4.jpg
15 		30 86 93:7
11 graphic file with name nihms64159t5.jpg
16 		graphic file with name nihms64159t6.jpg
17 		75 46 73:27
12d graphic file with name nihms64159t7.jpg
18 		graphic file with name nihms64159t8.jpg
19 		63 72 86:14
a

Reaction conditions: Cu(OTf)2 (0.2 equiv) and (R,R)-11a (0.2 equiv) were combined and treated with PhCF3 (0.1 M w/r to substrate) and heated at 50 °C for 1h. Substrate (1 equiv), MnO2 (3 equiv) and K2CO3 (1 equiv) were added and the reaction tube was sealed and heated at 120 °C for 24 h unless otherwise noted. All reactions were run at least two times to ensure reproducibility.

b

Yields refer to amount isolated after purification by flash chromatography on SiO2.

c

Enantiomeric excess and ratios were determined by chiral HPLC anlaysis (chiralcel OD-H or AD-RH).

d

Reactions were run for 96 h.