We have developed a formal [4+1] approach to pyrrolidines from readily available unactivated terminal alkenes as 4-carbon partners. The reaction provides a rapid construction of various pyrrolidine containing structures, especially for the diastereoselective synthesis of spiro-pyrrolidines. The reaction underwent smoothly with alkenes containing substituents at C4 and C5 positions, giving desired products in good yields. A variety of functional groups were well tolerated, providing corresponding products in moderate to good yields. The reaction was particularly efficient for the synthesis of spiro-pyrrolidines. It is also worth noting that greater than 20:1 diastereoselectivities were achieved regardless of trans/cis ratio of starting cyclohexanes. Mechanistic investigation suggests a Rh(III)-catalyzed intermolecular aziridination of the alkene and subsequent acid-promoted ring expansion for the pyrrolidine formation.

Rh(III)-catalyzed formal [4+1] approach to pyrrolidines from unactivated terminal alkenes and nitrene sources

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.