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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 2.

Nucleophile screen with BF3•OEt2

graphic file with name nihms91076f6.jpg
entry Nu–SiMe3 Na product cis:transb,c yield (%)d
1 7 1.8 2 8:92 82
2 8 6.2 3 8:92 87
3 9 8.2 4 50:50 88
4 10 9.0 5 58:42 80
5 11 10.2 6 60:40 86
a

N = nucleophilicity parameter; see ref 17.

b

Determined by GC and 1H NMR spectroscopic analysis of the unpurified reaction mixture.

c

Diastereoselectivities were independent of starting anomer ratio.

d

Isolated yield.