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. 2020 Sep 7;11(37):10119–10126. doi: 10.1039/d0sc02828b

Optimizations of reaction conditionsa.

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Entry Variation from standard conditions eeb (%) Yieldc (%)
1 None 92 88
2 L2 instead of L1 as ligand Trace
3 L3 instead of L1 as ligand 13 <5%
4 L4 instead of L1 as ligand Trace
5 L5 instead of L1 as ligand −80
6 L6 instead of L1 as ligand 72 33
7 Et3N instead of DBU as base 89 33
8 DABCO instead of DBU as base 88 35
9 TBD instead of DBU as base 86 37
10 1,4-dioxane instead of THF as solvent 91 86
11 Toluene instead of THF as solvent 87 64
12 –OBz instead of –OCOOMe 93 38
13 –Cl instead of –OCOOMe –3 46
14 –OPO(OEt)2 instead of –OCOOMe 50 42
15 –OBoc instead of –OCOOMe 89 34
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a

Reaction conditions: all reactions were run on 0.1 mmol scale with respect to 1.

b

ee determined by chiral HPLC.

c

Isolated yield. DABCO = 1,4-diazabicyclo[2.2.2]octane, DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene, TBD = 1,5,7-triazabicyclo[4.4.0]dec-5-ene.