Skip to main content
. 2020 Mar 11;11(15):3852–3861. doi: 10.1039/d0sc00475h

Scope of anti-selective Michael addition.

graphic file with name d0sc00475h-u4.jpg
Entry 1 2: R2 T (d) anti-5 Yielda (%) drb eec (%)
1 1a 2a: 4-ClC6H4 2.5 anti-5a 99 15 : 1 95
2 1a 2b: 3-ClC6H4 2.5 anti-5b 99 14 : 1 95
3 1a 2c: 2-FC6H4 3 anti-5c 95 8 : 1 91
4 1a 2d: Ph 5 anti-5d 90 20 : 1 96
5 1a 2e: 4-MeC6H4 5 anti-5e 91 25 : 1 95
6 1a 2f: 2-naphthyl 5 anti-5f 99 22 : 1 95
7 1a 2g: 2-thienyl 5 anti-5g 97 20 : 1 97
8d 1a 2h: (E)-PhCH Created by potrace 1.16, written by Peter Selinger 2001-2019 CH 5 anti-5h 78 6 : 1 90
9 1b 2a: 4-ClC6H4 1.5 anti-5v 89 10 : 1 93
10 1c 2a: 4-ClC6H4 3 anti-5w 86 17 : 1 95
11 1d 2a: 4-ClC6H4 2 anti-5x 91 30 : 1 96
12 1e 2a: 4-ClC6H4 4 anti-5y 99 14 : 1 94
13e 1c 2m: CF3 3.5 anti-5q 88 11 : 1 94
14f 1d 2m: CF3 3.5 anti-5r 91 19 : 1 94
15e 1d 2n: CF2H 3 anti-5s 93 7 : 1 94
graphic file with name d0sc00475h-u5.jpg
a

Isolated yield.

b

Determined by 1H NMR analysis of the crude mixture.

c

Determined by HPLC analysis.

d

10 mol% 4b.

e

20 mol% 4b and 20 mol% K2HPO4·3H2O.

f

10 mol% 4b and 10 mol% K2HPO4·3H2O.

g

20 mol% 4b.