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

Scope of syn-selective Michael addition.

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Entry 1 2: R2 Time (d) syn-5 Yielda (%) drb eec (%)
1 1a 2a: 4-ClC6H4 7 syn-5a 76 7 : 1 93
2 1a 2b: 3-ClC6H4 8 syn-5b 79 7 : 1 93
3 1a 2c: 2-FC6H4 7 syn-5c 73 9 : 1 95
4 1a 2d: Ph 9 syn-5d 85 9 : 1 96
5 1a 2e: 4-MeC6H4 10 syn-5e 79 9 : 1 96
6 1a 2f: 2-naphthyl 7 syn-5f 81 8 : 1 93
7 1a 2g: 2-thienyl 7 syn-5g 85 10 : 1 96
8 1a 2h: (E)-PhCH Created by potrace 1.16, written by Peter Selinger 2001-2019 CH 8 syn-5h 76 15 : 1 94
9 1a 2i: (E)-4-BrC6H4CH Created by potrace 1.16, written by Peter Selinger 2001-2019 CH 5 syn-5i 70 13 : 1 93
10 1a 2j: (E)-3-FC6H4CH Created by potrace 1.16, written by Peter Selinger 2001-2019 CH 6 syn-5j 68 12 : 1 92
11 1a 2k: (E)-2-FC6H4CH Created by potrace 1.16, written by Peter Selinger 2001-2019 CH 8 syn-5k 81 12 : 1 94
12 1a 2l: (E)-2-MeC6H4CH Created by potrace 1.16, written by Peter Selinger 2001-2019 CH 9 syn-5l 80 13 : 1 94
13d 1b 2h: (E)-PhCH Created by potrace 1.16, written by Peter Selinger 2001-2019 CH 4 syn-5m 88 12 : 1 90
14 1c 2h: (E)-PhCH Created by potrace 1.16, written by Peter Selinger 2001-2019 CH 2 syn-5n 79 12 : 1 88
15d 1d 2h: (E)-PhCH Created by potrace 1.16, written by Peter Selinger 2001-2019 CH 4 syn-5o 72 13 : 1 93
16 1e 2h: (E)-PhCH Created by potrace 1.16, written by Peter Selinger 2001-2019 CH 8 syn-5p 69 14 : 1 95
17e 1c 2m: CF3 3 syn-5q 75 3 : 1 90
18e 1d 2m: CF3 2 syn-5r 76 4 : 1 92
19e 1d 2n: CF2H 6 syn-5s 52 2 : 1 87
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a

Isolated yield.

b

Determined by 1H NMR analysis of the crude reaction mixture.

c

Determined by HPLC analysis.

d

−20 °C.

e

5 Å MS was replaced by 20 mol% K2HPO4·3H2O.