Table 1.
Optimizations of reaction conditionsa.
![]() | ||||||
---|---|---|---|---|---|---|
Entry | R | Catalyst | Solvents | Yieldb (%) | drb (3a:4a) | eec (3a/4a, %) |
1 | PMP | A1 | toluene | 52 | 1:2.8 | 45/31 |
2 | PMP | A2 | toluene | 41 | 1:1 | 41/24 |
3 | PMP | A3 | toluene | 51 | 1.4:1 | 35/57 |
4 | PMP | A4 | toluene | 50 | 1.3:1 | 72/81 |
5 | PMP | A5 | toluene | 68 | 1:2.5 | 24/90 |
6 | PMP | B1 | toluene | 57 | 2.7:1 | 91/34 |
7 | PMP | B2 | toluene | 91 | 10:1 | 87/– |
8 | PMP | C1 | toluene | 51 | 1:11 | –/98 |
9 | Ar | B2 | toluene | 99 | 12:1 | 91/– |
10 | Ar | C1 | toluene | 80 | 1:9 | –/94 |
11 | Ar | B2 | CCl4 | 98 | 20:1 | 91/– |
12 | Ar | C1 | CCl4 | 85 | 1:12 | –/98 |
aReactions were performed with 1a (0.15 mmol), 2a (0.1 mmol), cat (0.01 mmol), 3 Å MS (100 mg), solvents (0.5 mL) at ambient temperature for 24 h.
bYields and dr value were determined by crude 1H NMR analysis using 1,2-dimethoxyethane (DME, 0.1 mmol) as internal standard.
cee values were determined by HPLC analysis on a chiral stationary phase. PMP = para-methoxylphenyl, Ar = 3,5-dimethoxyphenyl.