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. Author manuscript; available in PMC: 2011 Apr 14.
Published in final edited form as: J Am Chem Soc. 2010 Apr 14;132(14):5027–5029. doi: 10.1021/ja100185p

Table 1.

Reaction Optimization for Enantioselective Bicyclization.a

graphic file with name nihms-191220-t0003.jpg
entry catalyst additiveb solvent yield (%)c ee (%)d
1 2a, Ar = Ph (20 mol%) none MeCN 11 34
2 2a, Ar = Ph (20 mol%) TFA MeCH 16 35
3e 2a, Ar = Ph (20 mol%) TFA MeCH 42 42
4e 2b, Ar = 1-Np (20 mol%) TFA MeCH 56 74
5e 2b, Ar = 1-Np (20 mol%) TFA i-PrCN/DMEf 54 87
6e 2b, Ar = 1-Np (30 mol%) TFA i-PrCN/DMEf 70 87
a

Reactions peformed on a 0.20 mmol scale using 2.5 equiv of Cu(OTf)2 and 2.0 equiv of NaTFA.

b

3.0 equiv of TFA used.

c

Isolated yield.

d

ee determined by chiral HPLC analysis.

e

Slow addition of oxidant and base as a solution in MeCN or i-PrCN.

f

3:2 i-PrCN/DME (0.08 M).