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. Author manuscript; available in PMC: 2014 Aug 11.
Published in final edited form as: Angew Chem Int Ed Engl. 2011 Oct 6;50(47):11152–11155. doi: 10.1002/anie.201105557

Table 1.

Substrate Generality for the One-pot Tandem Epoxidation/Rearrangement Reaction.[a]

graphic file with name nihms553929t1.jpg

Entry 3 2, Ar 7 yield
(%)[b]
1 3-Me 4-NO2C6H4 7a 95
2 3-Me 3-NO2C6H4 7b 95
3 3-Me 2-NO2C6H4 7c 95
4 3-Me C6H5 7d 82
5 3-Me 4-CF3C6H4 7e 95
6 3-Me 4-BrC6H4 7f 90
7 3-Me 4-ClC6H4 7g 88
8 3-Me 4-FC6H4 7h 90
9 3-Me 4-MeC6H4 7i 81
10 3-Bn 4-NO2C6H4 7j 95
11 3-Bn 2-NO2C6H4 7k 95
12 3-Bn C6H5 7l 85
13 Me3-Me 4-NO2C6H4 7m 95[c]
[a]

The reaction was carried out with 3 (0.36 mmol), aldehyde (0.30 mmol), Rh2(OAc)4 (2 mol%), Cu(hfacac)2 (5 mol%), respective solvent (2 mL).

[b]

Isolated yield of 7 after chromatography.

[c]

The 1H NMR spectrum of the reaction mixture showed only one diasteroisomer, whose stereochemistry was confirmed by NOe analysis, see SI.