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. 2017 Aug 2;8(9):6686–6690. doi: 10.1039/c7sc02232h

Table 1. Catalyst identification and optimization of reaction conditions a .

Inline graphic
Entry Catalyst t [h] Yield [%] of 3aa b Yield [%] of 4aa b er of 4aa c
1 d None 6 90 90
2 None 48 <5
3 I 48 88 85 94.5 : 5.5
4 II 46 95 87 94 : 6
5 III 48 >99 86 92 : 8
6 IV 48 90 86 92 : 8
7 V 48 90 85 93 : 7
8 VI 48 >99 88 70 : 30
9 VII 24 >99 88 97.5 : 2.5
10 e , f VII 24 48 97.5 : 2.5
11 e , g VII 24 91 97.5 : 2.5

aReactions were carried out on a 0.1 mmol scale using 1.0 equiv. of 1a and 1.2 equiv. of 2a.

bYields correspond to the isolated product.

cThe enantiomeric ratio (er) was determined by HPLC analysis.

dReaction at 25 °C.

eUsing 2.0 equiv. of DBU.

fOne-pot reaction in 2-MeTHF. Time required for the 2nd step was 40 h.

gOne-pot reaction with solvent switch.