Table 1.
Entry | ECA conv. [%][b] |
Prod. | Carbomet./acyl. yield [%];[c] ECA yield [%][d] |
e.r.[e] | |
---|---|---|---|---|---|
1 | >98 | 3b | 40; 75 | 98:2 | |
2 | >98 | 3c | 63; 60 | 96:4 | |
3 | >98 | 3d | 80; 60 | 96.5:3.5 | |
4 | >98 | 3e | 80; 72 | 98:2 | |
5 | >98 | 3 f | 80; 60 | 98:2 | |
6 | >98 | 3g | 80; 54 | 96.5:3.5 | |
7 | >98 | 3h | 61; 51 | 97:3 | |
8 | >98 | 3i | 80; 55 | 90.5:9.5 | |
9 | >98 | 3j | 80; 60 | 94.5:5.5 |
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 1b was used as catalyst precursor.