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. 2021 Jul 29;11(42):26083–26092. doi: 10.1039/d1ra05297g

Scope of the Passerini reaction carried out in U/CC DES with chiral heterogeneous catalyst 11.

graphic file with name d1ra05297g-u3.jpg
Entry R1 in RCOOH 12 R2 in RCHO 13 R3 in RNC 14 Time (h) 15 Yielda (%) Eeb (%)
1 Ph; 12a Ph; 13a t-Bu; 14a 20 15a 87c 94.8
2 Ph; 12a 3-NO2C6H4; 13b t-Bu; 14a 24 15b 93 96.4
3 Ph; 12a 4-MeOC6H4; 13c t-Bu; 14a 20 15c 85 96.8
4 Ph; 12a 4-ClC6H4; 13d t-Bu; 14a 22 15d 93 96.9
5 Ph; 12a 4-MeC6H4; 13e t-Bu; 14a 24 15e 87 97.6
6 Ph; 12a PhCH Created by potrace 1.16, written by Peter Selinger 2001-2019 CH; 13f t-Bu; 14a 28 15f 86 92.7
7 Ph; 12a i-Pr; 13g t-Bu; 14a 20 15g 87 95.5
8 4-NO2C6H4; 12b Ph; 13a t-Bu; 14a 24 15h 84 95.6
9 4-MeOC6H4; 12c Ph; 13a t-Bu; 14a 30 15i 87 95.9
10 4-ClC6H4; 12d Ph; 13a t-Bu; 14a 20 15j 90 96.8
11 Me; 12e Ph; 13a t-Bu; 14a 20 15k 86 96.5
12 PhCH2; 12f Ph; 13a t-Bu; 14a 22 15l 87 93.1
13 3-Pyridyl; 12g 4-ClC6H4; 13d t-Bu; 14a 24 15m 78 96.5
14 Ph; 12a Ph; 13a 2-Naphthyl; 14b 20 15n 87 98.4
15 Ph; 12a 4-ClC6H4; 13d 2-Naphthyl; 14b 20 15o 83 95.3
16 Me; 12e 3-NO2C6H4; 13b 2-Naphthyl; 14b 24 15p 84 97.6
17 Me; 12e i-Pr; 13g 2-Naphthyl; 14b 22 15q 86 96.1
a

Yields refer to pure and isolated 15. Times and yields refer to the reactions carried out with 1 mmol of 12a, 13a, 14a with chiral catalyst 11 (5% mol).

b

Enantiomeric excess was determined by chiral analyses on HPLC (ee).

c

The same results were obtained using 10 mol% of catalyst 11.