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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 1.

Examination of Ketoimines Bearing Different N-aryl Groupsa

graphic file with name nihms-86754-t0001.jpg
entry G temp (°C) conv (%)b anti:synb er; ee (%)c
1 graphic file with name nihms-86754-t0002.jpg +4 68 <2:>98 63.5:36.5; 27
2 −15 45 <2:>98 67:33; 34
3 −30 20 <2:>98 64.5:35.5; 29
4 −78 <2 nd nd
5 graphic file with name nihms-86754-t0003.jpg −78 >98 93:7 95.5:4.5; 91
6 graphic file with name nihms-86754-t0004.jpg −78 >98 80:20 89.5:10.5; 79
7 graphic file with name nihms-86754-t0005.jpg −78 43 8:92 77.5:22.5; 55
a

Reactions performed under N2 atmosphere.

b

Conversion levels and diastereomeric ratios were determined by analysis of 400 MHz 1H NMR spectra of unpurified products.

c

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

nd = not determined.