Skip to main content
. 2022 Aug 24;144(35):16206–16216. doi: 10.1021/jacs.2c07969

Table 1. Optimization Studies.

graphic file with name ja2c07969_0009.jpg

entrya ligand additive 3 (%)b 4 (%)b 5 (%)b 6 (%)b
1 PPh3   <5 30 30 25
2 PCy3   15 42 23 14
3 IMes   24 36 19 <5
4 IPr   22 <5 5 <5
5 Xantphos   30 <5 30 <5
6 DPEphos   50 24 25 <5
7 dppf   35 14 12 <5
8 dppe   11 <5 <5 <5
9 dppp   40 18 20 <5
10 dcpe   25 16 12 <5
11 dcpe*c   60 <5 <5 15
12 dcpe P(O)Ph3 72 <5 <5 8
13 dcped   35 <5 <5 <5
14     <5 30 22 <5
15   P(O)Ph3 <5 8 6 <5
16e dcpe P(O)Ph3 60 <5 <5 10
17f dcpe P(O)Ph3 23 28 30 15
a

Reactions run on a 0.3 mmol scale. Diastereomeric ratio of 3 >95:5 in all cases.

b

Determined by 1H NMR analysis using 1,3,5-trimethoxybenzene as the internal standard.

c

dcpe* = dcpe:dcpe(O):dcpe(O)2 in a 3:1:3 ratio.

d

12 mol %.

e

NaOtBu used instead of LiOtBu.

f

NaOMe used instead of LiOtBu.