Table 2. Brønsted base screen for DAL with diene 13d, acid chloride 5, and (S)-(–)-BTM as catalyst.
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Entry | Base | de a (%) | ee b , c (%) | Conversion d (%) |
1 | Et3N | 71 | 60 | >95(60) |
2 | Pyridine | 76 | 85 | >95(46) |
3 | Hünig's base [EtN(iPr)2] | 71 | 65 | >95(55) |
4 | 2,6-Lutidine | 60 | 99 | >95(68) |
5 | 2,6-Di-tert-butylpyridine [DTBP] | 95 | 99 | >95(43) |
aDetermined by 1H NMR (500 MHz) analysis of crude reaction mixtures.
bDetermined by chiral HPLC analysis (see ESI for details).
cEnantiomeric excess of the major (–)-14f (endo) diastereomer (ee values for the exo diastereomer were similar).
dYields in parentheses refer to isolated, purified yields of cycloadducts.