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. Author manuscript; available in PMC: 2015 Jul 3.
Published in final edited form as: Org Lett. 2012 Mar 20;14(7):1704–1707. doi: 10.1021/ol300269u

Table 2.

Investigation of the rearrangement reaction.

graphic file with name nihms365478u3.jpg
entry conditions conversion
1 Bi(OTf)3(1.0 equiv) 0%
2 AcOH, then Bi(OTf)3 (0.05 equiv)a 100%
3 TMSCI, then Bi(OTf)3 (0.05 equiv)b 0%
4 AcSH, then Bi(OTf)3 (0.05 equiv)b 0%
5 CICH2CO2H, then Bi(OTf)3 (0.05 equiv) 100%
6 AcOH, then cat. TfOH 100%
7 AcOH at 35 °C, then Bi(OTf)3 (0.05 equiv) 100%(88%)c,d
a

40 h reaction time.

b

The product was the ring-opened DASP.

c

12 h reaction time.

d

Isolated yield with a dr > 19:1.