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. 2016 Oct 21;8(2):1511–1524. doi: 10.1039/c6sc04273b

Table 2. Brønsted base screen for DAL with diene 13d, acid chloride 5, and (S)-(–)-BTM as catalyst.

Inline graphic
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.