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. 2025 May 21;27(22):5720–5725. doi: 10.1021/acs.orglett.5c01478

2. Scope of Substrates Using (R)-3a or (R)-3b .

graphic file with name ol5c01478_0006.jpg

entry (R)-3 2: R, Ar 4 anti/syn ee (%)
1 3b 2b: 4-FC6H4, Ph 4ab >95/5 98
2 3b 2c: 4-ClC6H4, Ph 4ac >95/5 98
3 3b 2d: 4-BrC6H4, Ph 4ad >95/5 98
4 3a 2d 4ad >95/5 98
5 3a 2d 4ad >95/5 98
6 3a 2e: 4-CF3C6H4, Ph 4ae >95/5 99
7 3a 2f: 4-MeC6H4, Ph 4af 94/6 99
8 3b 2g: 3-MeC6H4, Ph 4ag >95/5 91
9 3a 2h: 3-FC6H4, Ph 4ah 91/9 92
10 3a 2i: 2-FC6H4, Ph 4ai >95/5 99
11 3b 2j: 2-naphthyl, Ph 4aj >95/5 98
12 3b 2k: 2-thiophenyl, Ph 4ak 83/17 92
13 3b 2l: Ph, 4-BrC6H4 4al 94/6 99
14 3b 2m: Ph, 4-MeC6H4 4am 93/7 95
15 3a 2n: cyclohexyl, Ph 4an 87/13 29, 18
16 3a 2a: Ph, Ph 4ca 73/27 90, 81
a

Reaction conditions: 1a (0.20 mmol), 2 (0.30 mmol), and (R)-3 (5 mol %) in Et2O (2 mL, 0.1 M) under a nitrogen atmosphere at 0 °C for 4 h unless otherwise specified.

b

Diastereomeric mixtures were formed quantitatively, and the diastereomeric ratio (anti/syn) was determined by 1H NMR measurements after short path silica-gel column chromatography.

c

The enantiomeric excess was determined by HPLC analysis using a chiral stationary phase column.

d

Gram-scale experiment: 1a (2.0 mmol), 2d (3.0 mmol), and (R)-3a (2.5 mol %, 0.05 mmol) in Et2O (20 mL, 0.1 M).

e

For 12 h.

f

A 63% combined yield of diastereoisomers.

g

Use 1c (0.20 mmol) instead of 1a for 16 h.