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. 2021 Apr 15;23(9):3248–3252. doi: 10.1021/acs.orglett.1c00620

Table 1. Screen of 3,3′-Substituted BINOL Ligands for the Enantioselective para-Claisen Rearrangement of Illicinole (3).

graphic file with name ol1c00620_0006.jpg

entry R temperature er of 2
1 H rt 46:54
2 Me rt 45:55
3 Ph rt 40:60
4 SiPh3 rt 57:43
5 2,6-dimethylphenyl rt 40:60
6 1-naphthyl rt 40:60
7 9-anthracenyl rt 30:70
8 9-anthracenyl –40 °C 26:74
9 9-anthracenyl –60 °C nr
10 neopentyl rt 76:24
11 neopentyl –40 °C 87:13
12 neopentyl –60 °C nr
13 methylene-1-adamantyl –20 °C 84:16
14 methylene-1-adamantyl –40 °C nr