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. 2016 Oct 6;55(42):13180–13183. doi: 10.1002/anie.201607731

Table 1.

Optimization: cation‐directed enantioselective C‐acylation.[a] Inline graphic

Entry R1 Catalyst Base e.r.[b]
1 Ph Bu4NBr K2CO3 (aq.)[c] 50:50
2 Ph 10 K2CO3 (aq.)[c] 56:44
3 Ph 10 KOH (aq.)[c] –
4 Ph 10 KOH (s) 59:41
5 Ph 11 KOH (s) 69:31
6 Ph 11 NaOPh (s) 51:49
7 C6F5 11 KOH (s) 42:58
8 C6F5 12 KOH (s) 79:21
9 C6F5 13 KOH (s) 25:75
10 C6F5 14 KOH (s) 36:64
11 C6F5 15 KOH (s) 29:71
12 C6F5 16 KOH (s) 17:83
13 C6F5 17 KOH (s) 88:12
14 C6F5 17 K3PO4 (s) 89:11
15 C6F5 17 K3PO4 (aq.)[c] 97:3
 
graphic file with name ANIE-55-13180-g004.jpg

[a] Conditions: substrate 7 or 8 (0.02 mmol), catalyst (10 mol %), solid base (1.0 equiv.), PhMe ([substrate]=0.1 mol dm−3), RT, 48 h. [b] e.r. determined by chiral stationary phase HPLC. [c] base: 50 % aq., w/w, 10.0 equiv.