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. Author manuscript; available in PMC: 2022 Sep 30.
Published in final edited form as: Chem Commun (Camb). 2021 Sep 30;57(78):10099–10102. doi: 10.1039/d1cc03515k

Table 1.

Effect of Reaction Conditionsa

graphic file with name nihms-1740653-t0005.jpg
Entry Substrate Ligand Yield (%) ee 2 (%)

1 1a 3a 30b --
2c 1a 3a 48 --
3c 1a 3c 62 60
4c,d 1a 3c 50 89
5c,d,e 1a 3c 68 71
6 1b 3a 47 --
7 1b 3b 78 >95
8 1b 3c 64 94
9 1b 3c 47 Nd
10d 1b 3c 78 >95
11d,f 1b 3c 75 >95
12d,g 1b 3c 48 Nd
13 1b 3d 84 −89
14 1b 3e 81 −84
15d 1b 3d 78 >−95
a

General conditions: 1 (0.18 mmol), 20 mol% Cu(OTf)2, 25 mol% 3, PhCF3 (0.1 M w/r to 1), 120 °C, 24 h, sealed tube, under Argon. MnO2 (85% by weight, <5 m particle size) was used.

b

30% product 2a along with 30% 1a and 33% of its corresponding aldehyde.

c

Ag2CO3 (1 equiv) was used instead of MnO2.

d

Reaction run in 1,2-dichloroethane (DCE) at 105 °C.

e

Reaction run with 2,6-di-tert-butyl-4-methylpyridine instead of K2CO3.

f

15 mol% Cu(OTf)2 and 19 mol% 3c were used.

g

10 mol% Cu(OTf)2 and 12.5 mol % 3c were used. Nd = not determined.