Table 1.
Condition evaluation of the reactiona
![]() | ||
---|---|---|
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.