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Stereospecific ring expansion of chiral vinyl aziridines.

ABSTRACT: In this report, it is demonstrated that chiral vinyl aziridines can be stereospecifically ring expanded. This synthetic approach allows controlled access to chiral 2,5-cis- or 2,5-trans-3-pyrroline products from starting materials with the appropriate aziridine geometry. Twenty three ring expansion examples, most of which feature a stereospecific cyclization, are presented.

SUBMITTER: Brichacek M 

PROVIDER: S-EPMC3072884 | biostudies-literature | 2011 Mar

REPOSITORIES: biostudies-literature

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Stereospecific ring expansion of chiral vinyl aziridines.

Brichacek Matthew M   Villalobos Mauricio Navarro MN   Plichta Alexandra A   Njardarson Jon T JT  

Organic letters 20110210 5

In this report, it is demonstrated that chiral vinyl aziridines can be stereospecifically ring expanded. This synthetic approach allows controlled access to chiral 2,5-cis- or 2,5-trans-3-pyrroline products from starting materials with the appropriate aziridine geometry. Twenty three ring expansion examples, most of which feature a stereospecific cyclization, are presented. ...[more]