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. Author manuscript; available in PMC: 2011 Jul 16.
Published in final edited form as: Org Lett. 2010 Jul 16;12(14):3222–3225. doi: 10.1021/ol101144k

Table 1.

Optimization of Catalytic Reaction Conditionsa

graphic file with name nihms214548t1.jpg
entry x solvent/additive (equiv) % yield (12:13)b
1 25 CH2Cl2 / none 72; 5:1c
2 20 MeNO2 / none 94; 3.7:1
3 10 MeNO2 / Bu4NPF6 (2) 97; 3.3:1d
4 2 MeNO2 / Bu4NPF6 (2) 85; 2.8:1
5 20 MeNO2 / Bu4NPF6 (0.2) 93; 3.6:1d
6 0 MeNO2 / Bu4NPF6 (2) -e
7 0 MeNO2 / TfOH (0.2) 87; 2.5:1d
8 20 MeNO2 / Bu4NPF6 (0.2)/
DTBMP (1)		 -e
9 20 MeNO2 / Bu4NPF6 (0.2)/
3 Å MS		 -e
a

All reactions conducted at 0 °C to rt for 2 h unless otherwise noted.

b

Isolated yield and ratios.

c

rt, 17 h.

d

time = 30 min.

e

no reaction. DTBMP = 2,6-di-tert-butyl-4-methylpyridine.