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. Author manuscript; available in PMC: 2012 Apr 15.
Published in final edited form as: J Org Chem. 2011 Mar 14;76(8):2577–2584. doi: 10.1021/jo102448n

Table 1.

Oxidative dearomatization employing sparteine surrogates.a

graphic file with name nihms280784u3.jpg
entry ligand product yieldb (ee)
1 graphic file with name nihms280784t1.jpg
4 		graphic file with name nihms280784t2.jpg
(R)-11 		84% (98%)2
2 graphic file with name nihms280784t3.jpg
5 		graphic file with name nihms280784t4.jpg
(S)-11 		63% (92%)
3 graphic file with name nihms280784t5.jpg
6 		graphic file with name nihms280784t6.jpg
(S)-11 		70% (95%)
4 graphic file with name nihms280784t7.jpg
7 		graphic file with name nihms280784t8.jpg
(S)-11 		54% (74%)
5 graphic file with name nihms280784t9.jpg
8 		graphic file with name nihms280784t10.jpg
(R)-11 		33% (11%)
a

Conditions: (a) 2.2 equiv. Cu(CH3CN)4PF6, 2.4 equiv. ligand, 1.6 equiv. DIEA, 2.4 equiv. DMAP, O2, −78°C to −10°C; (b) aq. H2PO4/K2HPO4 buffer (pH 7.2), CH3CN, RT [b] Isolated yield after silica gel chromatography. DIEA = N,N-diisopropylethylamine, DMAP = 4-(dimethylamino)pyridine.