Table 1. Initial Screening of Different NHC–Cu Complexesa.
entry | imidazolinium salt | conv (%)b | yield (%)c | SN2′:SN2b | erd |
---|---|---|---|---|---|
1 | 4 | 38 | 31 | 67:33 | 45:55 |
2 | 5 | 76 | 59 | 79:21 | 74:26 |
3 | 6 | 38 | 30 | >98:2 | 78:22 |
4 | 7 | 91 | 90 | >98:2 | 41:59 |
5 | 8 | 72 | 70 | 98:2 | 34:66 |
6 | 9a | 98 | 93 | 98:2 | 87:13 |
7 | 9b | 97 | 97 | 98:2 | 92:8 |
Reactions performed under N2 atm.
Conversion (allylic phosphate consumption) and site selectivity (±2%) were determined by analysis of 400 MHz 1H NMR spectra of product mixtures prior to purification.
Yield of products (±5%) after purification by silica gel chromatography.
Enantioselectivity (±2%) determined by HPLC analysis. See the Supporting Information for experimental and analytical details.