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. Author manuscript; available in PMC: 2010 Dec 7.
Published in final edited form as: J Org Chem. 2009 Dec 4;74(23):9222–9224. doi: 10.1021/jo902089e

Table 1.

Cyclization of Methyl diazo(2-phenylmethyleneaminophenyl)acetate Catalyzed by Lewis Acids

graphic file with name nihms159021t1.jpg
entry Lewis acid 1
mol%
reaction time
(min)
yield (%)
1 ZnCl2 60 very low
conversion
2 BF3•Et2O 10 100
3 TiCl4 5 100
4 SnCl4 10 100
5 Mg(OTf)2 60 no conversion
6 Sn(OTf)2 15 100
7 In(OTf)3 5 100
8a Zn(OTf)2 40 100
9 Ni(OTf)2 15 100
10 Cu(OTf)2 5 100
11 Sc(OTf)3 5 100
12 La(OTf)3 60 very low
conversion
13 Yb(OTf)3 20 100
a

Reaction was complete in less than 10 min when 5 mol% Zn(OTf)2 was used; reaction was complete in 10 h when 0.1 mol% Zn(OTf)2 was used.