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. 2015 Sep 7;54(44):13007–13011. doi: 10.1002/anie.201505628

Table 1.

Enantiomeric excesses of Diels–Alder products using different copper catalyst assemblies[a]

Ligand a b c d e
2 13 32 31 (90:10)[b] 72 (90:10)[b]
CB [6] 0 2
CB [7] 1 9 10 13 55
CB [8] 0 12 32 73 (96:4)[b] 92 (97:3)[b]

[a] General conditions: 1 a (1.5 μmol), 2 (4 μL), Cu2+ (3 % mol), ae (4.5 % mol), CB[n] (6 % mol) in 1 mm phosphate buffer (PBS) with pH 7.4, for 24 h at 6 °C. Data were obtained from the crude product on chiral phase HPLC. The ee values are averaged over two experiments and are reproducible within ±2 %. [b] Endo/exo ratios are in parentheses. In all reactions, conversions determined by HPLC are >99 %. The absolute configuration of the main products were identified as the (2R,3R)-enantiomer.