Table 2.
Entry | ECA conv. [%][b] |
Prod. | Carbomet./acyl. yield [%];[c] ECA yield [%][d] |
e.r.[e] | |
---|---|---|---|---|---|
1 | >98 | 4a | 80; 82 | 99:1 | |
2 | >98 | 4b | 40; 95 | 97.5:2.5 | |
3 | >98 | 4c | 88; 88 | 99:1 | |
4 | 88 | 4d | 60; 48 | 99:1 | |
5 | >98 | 4e | 80; 95 | 98:2 | |
6 | >98 | 4 f | 80; 80 | 97:3 | |
7 | >98 | 4g | 80; 97 | 98:2 | |
8 | >98 | 4h | 80; 71 | 99:1 | |
9 | >98 | 4i | 40; 81 | 98:2 | |
10 | >98 | 4j | 63; 95 | 99:1 | |
11 | >98 | 4k | 62; 87 | 95:5 | |
12 | >98 | 4l | 80; 85 | 97.5:2.5 | |
13 | >98 | 4m | 61; 83 | 92:8 |
Reactions were performed under N2 atmosphere; enones generated with >98% E selectivity in all cases.
Determined by analysis of 400 MHz 1H NMR spectra of unpurified mixtures (±2%).
Yield of isolated and purified products (±5%).
Determined by HPLC analysis; see the Supporting Information for details.
NHC-Ag complex 1a was used as catalyst precursor.
TBS = tert-butyl-(dimethyl)silyl.