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. 2014 Sep 1;136(37):12872–12875. doi: 10.1021/ja5075163

Table 2. Effect of Et3Na,b.

graphic file with name ja-2014-075163_0009.jpg

entry catalyst (mol%) additive (mol%) yield (%) ee (%)
1 2 (10) none 70 88
2 2·HCl (10) none 21 18
3 2·HCl (10) Et3N (50) 76 84
4 2 (10) Et3N (50) 95 99
5 2 (10) Et3N (25) 96 99
6 2 (5) Et3N (25) 83 94
7c 2 (10) Et3N (50) 70 93
a

Conditions: substrate (0.05 mmol), catalyst (10 mol%), diketone (0.1 mmol), DCM (1 mL), under N2, initially cooled to −78 °C and stirred at −0 °C, 36 h.

b

The yield was determined by the 1H NMR analysis of the crude product using CH2Br2 as the internal standard.

c

Reaction carried out in the absence of added 4 Å MS.