Dual Rh(II)/Pd(0) Relay Catalysis Involving Sigmatropic Rearrangement Using N-Sulfonyl Triazoles and 2-Hydroxymethylallyl Carbonates

Liang Zhu Huang, Zi Xuan, Jong Un Park, Ju Hyun Kim

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

Dual Rh(II)/Pd(0) relay catalysis of N-sulfonyl triazoles and 2-hydroxymethylallyl carbonates has been developed, which affords N-sulfonyl pyrrolidines in moderate to good yields with high diastereoselectivities. The reaction proceeds via a relay mechanism involving O-H insertion onto the α-imino Rh(II)-carbene, [3,3]-sigmatropic rearrangement, dipole formation through Pd(0)-catalyzed decarboxylation, and intramolecular N-allylation, leading to the formation of multiple bonds in a one-pot operation.

Original languageEnglish
Pages (from-to)6951-6956
Number of pages6
JournalOrganic Letters
Volume24
Issue number38
DOIs
StatePublished - 30 Sep 2022

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