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. Author manuscript; available in PMC: 2010 Nov 15.
Published in final edited form as: J Am Chem Soc. 2008 Jan 31;130(8):2416–2417. doi: 10.1021/ja710521m

Table 1.

Optimization of Conditions

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entry azolium salt temp (°C) yielda (%) drb eec (%)
1 A 0 75d 4:1
2 B 0 46d 8:1 −65
3 C 0 52d 8:1 −33
4 D 0 51d 8:1 87
5 D −25 49d 20:1 93
6 De −25 70f 20:1 93

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a

Isolated yields.

b

Diastereomeric ratio determined by 500 MHz NMR spectroscopy.

c

Enantiomeric excess determined by HPLC Chiracel AD-H.

d

2:1 ratio of 1a to 2a.

e

20 mol % of D, Et3N used instead of DBU.

f

2:1 ratio of 2a to 1a, NaOMe/MeOH used in place of DBU/MeOH.