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An aza-Prins cyclization approach to functionalized indolizidines from 2-allylpyrrolidines.

ABSTRACT: The stereoselective synthesis of a diverse set of functionalized indolizidine systems has been accomplished through the aza-Prins cyclization of 2-allylpyrrolidines. The condensation of aldehydes onto 2-allylpyrrolidines yields iminium ions that undergo highly diastereoselective aza-Prins cyclization, producing up to two stereogenic centers and two new rings in one step.

SUBMITTER: Liu X

PROVIDER: S-EPMC3492938 | biostudies-literature | 2012 Nov

REPOSITORIES: biostudies-literature

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An aza-Prins cyclization approach to functionalized indolizidines from 2-allylpyrrolidines.

Liu Xiaoxi X McCormack Michael P MP Waters Stephen P SP

Organic letters 20121025 21

The stereoselective synthesis of a diverse set of functionalized indolizidine systems has been accomplished through the aza-Prins cyclization of 2-allylpyrrolidines. The condensation of aldehydes onto 2-allylpyrrolidines yields iminium ions that undergo highly diastereoselective aza-Prins cyclization, producing up to two stereogenic centers and two new rings in one step. ...[more]

PMID: 23098169

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