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Communication | Special issue | Vol 80, No. 2, 2010, pp.773-778
Published online, 16th September, 2009
DOI: 10.3987/COM-09-S(S)73
Facile Synthesis and Ring-Opening of 4-(Tributylstannyl)pyrrolidine-2-carboxylates

Makoto Shimizu,* Hiromi Ando, Hitoshi Shibuya, and Iwao Hachiya

*Department of Chemistry for Materials, Graduate School of Engineering, Mie University, 1577 Tsu, Mie 514-8507, Japan


On treatment of ethyl 2-(4-methoxyphenylimino)acetate with (E)-1-tert-butyldimethylsiloxy-3-tributylstannylalkenes in the presence of methanesulfonic acid (MsOH) at -78 °C, a ring-closing reaction proceeded to give 4-(tributylstannyl)pyrrolidine-2-carboxylates, while their ring-opening reaction was observed to give homoallylic amines under the influence of MsOH at -20 °C to room temperature.