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. Author manuscript; available in PMC: 2010 Sep 1.
Published in final edited form as: Tetrahedron. 2009 Sep 1;65(33):6447–6453. doi: 10.1016/j.tet.2009.05.066

Table 2.

Silylene transfer to α-keto esters with substitution at R3

graphic file with name nihms129834u2.jpg
Entry R1 R3 Product % Yield d.r.
1 Me Ph 2a 70 ≥97:3
2 Ph Me 2f 62 ≥97:3
3 Ph n-Bu 2g 72 ≥97:3
4 Ph CH2OTBDMS 2h 71 ≥97:3
5 Et (CH2)2OBn 2i 75 ≥97:3

Conditions: α-keto ester (1.0 equiv), silacyclopropane 2 (1.5 equiv), AgOTs (0.10 equiv), toluene, −25 °C, 16 h then, HF·Pyr (4.0 equiv), isolated yields.