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. Author manuscript; available in PMC: 2013 Apr 1.
Published in final edited form as: Nat Chem. 2012 Sep 16;4(10):817–824. doi: 10.1038/nchem.1450

Table 1.

Reaction optimisation.a

graphic file with name nihms399652u1.jpg
entry catalyst acid yield (%)b ee (%)c
1 3b HCl 10 5
2 3b HOTf 73 32
3 3b FSO3H 78 19
4 3b 2,4-diNBSA 79 63
5 3b 4-NBSA 72 73
6 4-NBSA 7 n/a
7 3a 4-NBSA 16 12
8 3c 4-NBSA 84 84
9 3d 4-NBSA 80 85
10 3e 4-NBSA 93 93
11 3f 4-NBSA 91 91
12 3g 4-NBSA 97 88
13 4e 4-NBSA 98 92
a

Optimisation reactions were performed on 0.05 mmol scale.

b

Isolated yields of material purified chromatographically.

c

Enantiomeric excesses (ee’s) determined by HPLC analysis.

MS = molecular sieves; 2,4-diNBSA = 2,4-dinitrobenzenesulfonic acid; 4-NBSA = 4-nitrobenzenesulfonic acid.