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. Author manuscript; available in PMC: 2010 Jan 21.
Published in final edited form as: J Am Chem Soc. 2009 Jan 21;131(2):570–576. doi: 10.1021/ja8062315

Table 2.

Ag-Catalyzed AVM of Aryl-Substituted α-Ketoimine Estersa

graphic file with name nihms-86754-t0006.jpg
 
  
  
 NaHC03 workup (−78 °C→22 °C)
 HOAc workup (−78 °C→22 °C)
entry Ar substrate 7:8b yield 7 (%)c 7 er; ee (%)d 7:8b yield 7 (%)c 7 er; ee (%)d
1 C6H5 4a 93:7 72 95.5:4.5; 91 95:5 88 96:4; 92
2 m-OMeC6H4 4b 80:20 76 93:7; 86 95:5 95 96.5:3.5; 93
3 m-ClC6H4 4c 75:25 51 90.5:9.5; 81 92:8 72 93.5:6.5; 87
4 p-BrC6H4 4d 88:12 78 96:4; 92 95:5 80 96:4; 92
5 p-IC6H4 4e 86:14 62 95:5; 90 >98:<2 81 96.5:3.5; 93
6 p-t-BuC6H4 4f 75:25 68 93:7; 86 89:11 77 95:5; 90
7 p-CF3C6H4 4g 89:11 67 95.5: 4.5; 91 95:5 87 97:3; 94
8 2-naphthyl 4h 93:7 68 95:5; 90 >98:<2 81 95.5:4.5; 91
9 o-BrC6H4 4i <2:>98 87e 66:34; 32e <2:>98 87e 66:34; 32e
a

Reactions performed under N2 atmosphere; >98% conversion in all cases (substrate consumption based on internal standard).

b

Diastereomeric ratios were determined by analysis of 400 MHz 1H NMR spectra of the unpurified reaction mixtures.

c

Yields are of the purified anti-7.

d

Enantiomer ratio (er) values were determined by chiral HPLC analysis; see the Supporting Information for details.

e

Data for syn-8i as the major isomer.