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. Author manuscript; available in PMC: 2012 Aug 17.
Published in final edited form as: J Am Chem Soc. 2011 Jul 22;133(32):12458–12461. doi: 10.1021/ja205674x

Table 1.

Isomerization of 8a to 9a catalyzed by cinchona alkaloidsa

graphic file with name nihms312905t1.jpg
entry catalyst T(°C) Time conv.(%)b ee(%)b
1 1a rt 4h 80 47c
2 2a rt 4h 0 -
3 2b rt 4h 20 32
4 4 rt 4h 0 -
5 5 rt 4h 0 -
6 2 + 5 rt 4h <5 0
a

Unless noted, reactions were run with 0.05 mmol of 8a in 0.05 mL of CH2Cl2 with 10 mol% catalyst. See supporting information for details.

b

Determined by HPLC analysis.

c

10 min, 20% conv., 67% ee.