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. Author manuscript; available in PMC: 2010 Feb 24.
Published in final edited form as: J Am Chem Soc. 2005 May 4;127(17):6170–6171. doi: 10.1021/ja043884l

Table 1.

Reaction Scope with 1aa

graphic file with name nihms176022e1.jpg (1)
entry R′ R yield (%)b 2:3c
1 Ph Ph 77 78:22
2 n-C6H13 Ph 77 74:26
3 BnOCH2 Ph 60 72:28
4 PhthNCH2 Ph 48 71:29
5 Me3Si Ph 81 76:24
6 Me3Si 2-(Me)C6H4 65 80:20
7 Me3Si 4-(MeO)C6H4 73 80:20
8 Me3Si 4-(Cl)C6H4 76 78:22
9 Me3Si 2-furyl 66 47:53
10 Me3Si (E)-PhCHd=CH 77 53:47
a

Reaction carried out using 1.0 equiv of 1a, 3.0 equiv of alkyne, 1.5 equiv of PhCHO, 3.0 equiv of ZnI2, and 3.3 equiv of Et3N for 24–48 h.

b

Average of two isolated yields. All reported yields are for two steps.

c

Determined by 1H NMR analysis of the crude reaction. See Supporting Information for determination of relative stereochemistry.