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Concise synthesis of iminocyclitols via Petasis-type aminocyclization.

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.

SUBMITTER: Hong Z

PROVIDER: S-EPMC2900252 | biostudies-literature | 2009 Jun

REPOSITORIES: biostudies-literature

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Concise synthesis of iminocyclitols via Petasis-type aminocyclization.

Hong Zhangyong Z Liu Lei L Sugiyama Masakazu M Fu Yu Y Wong Chi-Huey CH

Journal of the American Chemical Society 20090601 24

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. ...[more]

PMID: 19530721

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