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. 2014 Nov 7;136(47):16485–16488. doi: 10.1021/ja510113s

Table 1. Reaction Optimizationa.

graphic file with name ja-2014-10113s_0005.jpg

entry [Se] acid cat. temp (°C) time (h) yield (%)b ee (%)c
1 NPSS HCl 4 rt 0.5 92 33(11d)
2 NPSS PyHCl 4 rt 2 85 36(36d)
3 NPSS PyHCl 5a rt 2 82 46
4 NPSS PyHCl 5b rt 2 82 60
5 NPSS PyHCl 5c rt 2 88 64
6 NPSS PyHCl 5d rt 2 84 67
7 NPSS PyHCl 5d –30 48 67 72
8 NPSS PyHCl 5d –45 48 <5 nd
9e NPSS PyHCl 5d –45 48 89 84
10e NPASS PyHCl 5d –45 48 85 87
11e NPASS PyHCl 5d –35 48 85 88
12e NPASS HCl 5d –35 48 87 88
a

Reactions conducted on 0.1 mmol scale.

b

Isolated yield of purified product.

c

Enantiomeric excess determined by HPLC analysis on commercial chiral columns.

d

ee after 12 h.

e

HMPA(S) (10 mol%) was added.