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. Author manuscript; available in PMC: 2009 Nov 6.
Published in final edited form as: Org Lett. 2008 Oct 10;10(21):4907–4910. doi: 10.1021/ol8019956

Table 4.

Effect of Nucleophile on Chemoselectivity

graphic file with name nihms91076f8.jpg
entry Nu1–SiMe3a Nu2–SiMe3a Lewis acid product ratiob
1 graphic file with name nihms91076t1.jpg graphic file with name nihms91076t2.jpg BF3•OEt2 3(4):6(96)
2 graphic file with name nihms91076t3.jpg graphic file with name nihms91076t4.jpg BF3•OEt2 4(25):6(75)
3 graphic file with name nihms91076t5.jpg graphic file with name nihms91076t6.jpg Me3SiOTf 4(13):6(87)
a

Five equivalents of nucleophile.

b

Determined by GC spectroscopic analysis of the unpurified reaction mixture