Abstract
A two-step method has been developed to synthesize several biologically important iminocyclitols in ca. 44-60% yields by using Petasis-type condensation. The method is very general and operationally simple, affording a series of iminocyclitols from easily available sugar derivatives. Unexpected diastereoselectivities are observed, suggesting that the condensation may proceed through a five- or six-membered cyclic iminium ion intermediate.
Publication types
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Research Support, N.I.H., Extramural
MeSH terms
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Amino Sugars / chemical synthesis
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Amino Sugars / chemistry
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Boronic Acids / chemistry
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Cyclitols / chemical synthesis*
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Cyclitols / chemistry
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Cyclization
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Imino Sugars / chemical synthesis
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Imino Sugars / chemistry
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Piperidines / chemical synthesis
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Piperidines / chemistry
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Pyrrolidines / chemical synthesis
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Pyrrolidines / chemistry
Substances
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Amino Sugars
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Boronic Acids
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Cyclitols
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Imino Sugars
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Piperidines
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Pyrrolidines