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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 2.

Cooperative Rhodium and Copper Catalyzed Bicyclization of Vinyldiazoacetates 3 with α,β-Unsaturated Aldehydes.[a]

graphic file with name nihms553929t2.jpg
entry 3 2, Ar / R’’ 8 dr[b]
(trans :cis)		 yield (%)[c]
1 3-Me C6H4 / H 8a 85:15 80
2 3-Me 4-MeOC6H4 / H 8b 75:25 87
3 3-Me 2-NO2C6H4 / H 8c 90:10 32
4 3-Bn C6H4 / H 8d 70:30 86
5 3-Bn C6H4 / C6H4 8e <5:95 65
[a]

Reaction in 0.3 mol scale: 3 (0.36 mmol), aldehyde (0.30 mmol), Rh2(OAc)4 (2 mol%), CuPF6 (5 mol%), solvent (2 mL).

[b]

Determined by 1H NMR of the crude reaction mixture.

[c]

Isolated yield of 8 (trans and cis) after chromatography.