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http://hdl.handle.net/2183/38499 Access to Pyrrolidine Imino Sugars via Tin(II)-Mediated Aldol Reactions of Bislactim Ethers: Synthesis of 2,5-Dideoxy-2,5-Imino-D-Glucitol
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O. Blanco, C. Pato, M. Ruiz and V. Ojea, Access to pyrrolidine imino sugarsvia tin(II)-mediated aldol reactions of bislactim ethers: synthesis of 2,5-dideoxy-2,5-imino-D-glucitol, Org. Biomol. Chem., 2008, 6, 3967–3969.
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[Abstract] 2,5-Dideoxy-2,5-imino-D-glucitol (DGDP) has been synthesized via the tin(II)-mediated anti-selective aldol reaction of bislactim ether 5 and a 3-O-silylated 2,4-ethylidene-D-erythrose derivative 6. In accordance with density functional theory calculations (at the B3LYP/cc-pVDZ-PP level), pericyclic transition structures with a boat-like conformation and a stabilizing hydrogen bond can account for the unexpected stereoselectivity.
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