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. Author manuscript; available in PMC: 2015 May 1.
Published in final edited form as: Chem Sci. 2014 Feb 14;5(5):1786–1793. doi: 10.1039/C4SC00237G

Table 5. Chiral 2-aminopyrrolidine formation via enantioselective alkene diamination.

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Entry Substrate Amine Nucleophile Product Ratio 6:7 Yield (%) 6 ee (%) 6
1a 5a TsNH2 6a, R1 = Me, R2 = Ts 67:33 64 >95
2b 5a TsNH2 6a, R1 = Me, R2 = Ts 76:24 72 >95
3c 5a SESNH2 6b, R1 = Me, R2 = SES 63:37 58 >95
4c 5a BsNH2 6c, R1 = Me, R2 = Bs 69:31 63 >95
5c 5a 2-MeC6H4SO2NH2 6d, R1 = Me, R2 = SO2(2-MeC6H4) 68:32 62 >95
6c 5a 4-MeOC6H4SO2NH2 6e, R1 = Me, R2 = SO2(4-MeOC6H4) 66:34 60 >95
7c 5a 4-ClC6H4SO2NH2 6f, R1 = Me, R2 = SO2(4-ClC6H4) 64:36 60 >95
8c 5a 4-NO2C6H4SO2NH2 6g, R1 = Me, R2 = SO2(4-NO2C6H4) 64:36 58 >95
9c 5a C3H5SO2NH2 6h, R1 = Me, R2 = SO2C3H5 67:33 61 >95
10c 5b TsNH2 6i, R1 = H, R2 = Ts 66:34 61 89

Conditions:

a

Using the (R,R)-Ph-box ligand (22 mol %) with 20 mol % Cu(OTf)2 and 4 equiv R2NH2.

b

Conditions (a) except using the (R,R)-Ph-box ligand (33 mol %) with 30 mol % Cu(OTf)2.

c

Conditions (a) except using the (4R,5S)-di-Ph-box ligand (22 mol %) with 20 mol % Cu(OTf)2.

d

Conditions (c) except using 5 equiv R2NH2. SES = 2-trimethylsilylethylsulfonyl, Bs = benzenesulfonyl.