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. 2024 Sep 24;146(40):27915–27924. doi: 10.1021/jacs.4c10698

Table 1. Condition Optimizationa.

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Entry Reaction partners L X Conv of 1a (%) Yield (%) of 3 (α:β)
1 α-1a and 2a L1 NTf2 99 89 (1:14.8)
2 L2 NTf2 99 87 (1:19.3)
3 L2 OTf 99 98 (1:1.6)
4 L3 NTf2 99 95 (1:10.2)
5 L4 NTf2 99 86 (1:12.8)
6 L5 NTf2 99 91 (1:13.2)
7 L6 NTf2 99 91 (1:11.7)
8 L7 NTf2 99 99 (1:9.9)
9 PPh3 NTf2 99 94 (1:6.3)
10 β-1a and 2a L2 NTf2 99 94 (4.2:1)
11 β-1a and 2b L2 NTf2 99 97 (7.4:1)
12 L2 OMs <5 N. D.
13 L2 OTs <5 N. D.
14 L2 BF4 38 35 (>20:1)
15 L2 PF6 99 84 (13.1:1)
16 L2 OTf 99 98 (15.4:1)
17 PPh3 OTf 99 96 (1:2.2)
18 L8 OTf 99 98 (1:1.8)
19 L2 BArF4 99 99 (1.7:1)
20 PPh3 BArF4 86 82 (1.8:1)
a

Reactions were carried out at 0.05 mmol scale. Yields and conversions (conv) were determined by 1H NMR analysis using 1,3,5-trimethoxybenzene as the internal standard. The ratios of 3a epimers were collected by the 1H NMR analysis of the crude reaction mixture. N. D. = not determined. Ad = 1-adamantyl. BArF4 = tetrakis[3,5-bis(trifluoromethyl)phenyl]borate.