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. 2023 Sep 2;14:5339. doi: 10.1038/s41467-023-40197-x

Table 1.

Condition evaluation of the reactiona

graphic file with name 41467_2023_40197_Taba_HTML.gif
Entry Variation from “standard condition” Yield of 3a (dr)b
1 None 88% (3.7:1)
2 (NH4)2CO3 instead of NH4OAc 41% (1:1.1)
3 NH4HCO3 instead of NH4OAc 41% (1:1.1)
4 NH2CO2NH4 instead of NH4OAc 39% (1:1.2)
5 NH4Cl instead of NH4OAc trace
6 NH4BF4 instead of NH4OAc trace
7 Catalyst A instead of Catalyst C 61% (2.1:1)
8 Catalyst B instead of Catalyst C 54% (3.6:1)
9 w/o LiBF4 80% (2.6:1)
10c Sc(OTf)3 instead of LiBF4 56% (3.3:1)
11c Zn(OTf)2 instead of LiBF4 73% (3.7:1)
12 2,6-tBu2pyridine instead of LiBF4 88% (2.7:1)
13 2,6-lutidine instead of LiBF4 82% (2.5:1)
14 collidine instead of LiBF4 69% (2.9:1)
15 w/o PC, w/o light N.D.

aThe reaction was conducted using 1a (0.1 mmol), 2a (0.2 mmol) under indicated conditions.

bYield and diastereomeric ratio (dr) were determined by 1H NMR of crude mixture of the reaction using PhTMS as internal standard.

cAdditive (20 mol%) was used.