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Diastereoselective [3 + 2] Cycloaddition between Tertiary Amine N-Oxides and Substituted Alkenes to Access 7-Azanorbornanes.

ABSTRACT: We have developed a diastereoselective synthesis of 43 novel 7-azanorbornanes using tertiary amine N-oxides and substituted alkenes. Our method uses an efficient [3 + 2] cycloaddition, starting from either commercially available or easily accessible precursors to generate yields up to 97% and diastereomeric ratios up to >20:1. Density functional theory (DFT) calculations were performed, suggesting that the observed diastereoselectivity is likely due to steric considerations.

SUBMITTER: Cocolas AH

PROVIDER: S-EPMC11320637 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature

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Diastereoselective [3 + 2] Cycloaddition between Tertiary Amine <i>N</i>-Oxides and Substituted Alkenes to Access 7-Azanorbornanes.

Cocolas Alexander H AH Lane Aiden M AM Musiak Benjamin S BS Chartier Eric J EJ Bedillion Derek A DA Hejnosz Sarah L SL Rohde Jeffrey J JJ Lummis Paul A PA Evanseck Jeffrey D JD Montgomery Thomas D TD

Organic letters 20240722 31

We have developed a diastereoselective synthesis of 43 novel 7-azanorbornanes using tertiary amine <i>N</i>-oxides and substituted alkenes. Our method uses an efficient [3 + 2] cycloaddition, starting from either commercially available or easily accessible precursors to generate yields up to 97% and diastereomeric ratios up to >20:1. Density functional theory (DFT) calculations were performed, suggesting that the observed diastereoselectivity is likely due to steric considerations. ...[more]

PMID: 39038111

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