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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 3.

Nucleophile Screen with Acetal 12.

graphic file with name nihms91076f7.jpg
entry Nu–SiMe3 Na product cis:transb,c yieldd
1 7 1.8 13 1:99 67
2 8 6.2 14 2:98 83
3 9 8.2 15 17:83 93
4 11 10.2 16 34:66 69
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.