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. 2021 Jan 5;143(2):675–680. doi: 10.1021/jacs.0c12042

Table 1. Reaction Developmenta.

graphic file with name ja0c12042_0003.jpg

entry catalyst T (°C) conv. (%) yield 2a (%) isom. (%) er
1 3 80 41 34 5 54:46
2 4 80 47 30 trace 44:56
3 5 80 13 <10 trace 53:47
4 6 80 55 45 9 47:53
5 7a 80 95 90 trace 49:51
6 7b 80 full 93 56:44
7 7c 80 full 85 88:12
8 7d 80 full 93 88:12
9 7e 80 full 93 90:10
10b 7e 60 full 95 95:5
a

Reactions were performed with substrate 1a (0.02 mmol), catalyst (2 mol %) in methylcyclohexane (CyMe, 0.2 mL); conversions (conv.), yields of 2a, and olefin isomerizations (isom.) were determined by 1H NMR analysis with mesitylene as an internal standard; enantiomeric ratios (er’s) were measured by HPLC. When the reaction was not carried out in the dark, byproducts and lower yields were observed.

b

48 h.