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. 2014 Nov 12;6(2):1219–1224. doi: 10.1039/c4sc02610a

Table 1. Effect of the porphyrin ligand on the stereoselective metalloradical C–H alkylation of α-methoxycarbonyl-α-diazosulfone 1a catalyzed by [Co(D 2-Por*)] a .

Inline graphic
Entry Catalyst (loading) Yield b (%) dr c ee d (%)
1 [Co(TPP)] (120 mol%) NR e
2 [Co(P1)] (2 mol%) 83 95 : 5 –24
3 [Co(P2)] (2 mol%) 63 96 : 4 91
4 [Co(P3)] (2 mol%) 92 96 : 4 92
graphic file with name c4sc02610a-u2.jpg

aReactions were carried out at room temperature for 72 h in a one-time fashion without slow addition of the diazo reagent using [Co(Por)] under N2.

bIsolated yields.

cThe trans : cis diastereomeric ratio determined by 1H-NMR.

dEnantiomeric excess determined by chiral HPLC.

eNo reaction.

fFor clarity, the other two meso-groups of the porphyrin are omitted.