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. 2020 Nov 2;11:5527. doi: 10.1038/s41467-020-19294-8

Table 1.

Optimizations of reaction conditionsa.

graphic file with name 41467_2020_19294_Figa_HTML.gif
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.