Fig. 3: Reaction scope of 1,3-enyne-tethered cyclohexadienones. | Nature Communications

Fig. 3: Reaction scope of 1,3-enyne-tethered cyclohexadienones.

From: Copper(I)-catalyzed diastereo- and enantio-selective construction of optically pure exocyclic allenes

Fig. 3

aConditions A: Reactions were performed using 1,3-enyne 1 (0.2 mmol), PMHS (2.2 equiv), CuCl (5 mol%), (R,R)-Ph-BPE (6 mol%), t-BuONa (7.5 mol%), and t-BuOH (1.2 equiv) in DCE (2 mL) under Ar atmosphere, -30 °C. bYield of isolated product. cDetermined by 1H NMR analysis of unpurified mixtures. dDetermined by HPLC analysis using a chiral stationary phase. eDMMS (1.8 equiv), rt. fPMHS (5.0 equiv), -15 °C. gConditions B: Reactions were performed using 1,3-enyne 4 (0.2 mmol), PMHS (2.2 equiv), CuCl (5 mol%), (R,R)-Ph-BPE (6 mol%), and t-BuONa (7.5 mol%) in DCE (2 mL) under Ar atmosphere, −30 °C, then work-up with NH4F (0.5 M in MeOH). hDMMS (1.5 equiv) was used instead of PMHS.

Back to article page