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. Author manuscript; available in PMC: 2009 Nov 6.
Published in final edited form as: Org Lett. 2008 Sep 25;10(21):4839–4842. doi: 10.1021/ol8019204

Table 2.

Prins Cyclization with Aromatic Aldehyde and O3ReOSiPh3

graphic file with name nihms86406t2.jpg
entry aldehyde time (h) yield (%)
1 graphic file with name nihms86406t3.jpg 24 82
2a graphic file with name nihms86406t4.jpg 25 88b
3 graphic file with name nihms86406t5.jpg 27 75
4a graphic file with name nihms86406t6.jpg 26 89b
5a graphic file with name nihms86406t7.jpg 50 58
6 graphic file with name nihms86406t8.jpg 18 84
7 graphic file with name nihms86406t9.jpg 168 30d
8c graphic file with name nihms86406t10.jpg 23 83
9 graphic file with name nihms86406t11.jpg 24 73
10 graphic file with name nihms86406t12.jpg 24 55
a

Enantiomeric series (11-S alcohol, 99% ee).

b

97% ee by HPLC analysis.

c

10 mol % O3ReOSiPh3.

d

Starting material was also recovered in 11% yield.