Nitroalkene [4 + 2] Cycloaddition as a General and Stereoselective Route to the Synthesis of 3,3- and 3,4-Disubstituted Pyrrolidines

Scott E. Denmark, Lawrence R. Marcin

Research output: Contribution to journalArticlepeer-review

Abstract

2,2-Disubstituted 1-nitroalkenes 12 undergo Lewis acid-promoted [4 + 2] cycloadditions with n-butyl vinyl ether to afford cyclic nitronates 14 as anomeric mixtures in good yields. The resulting nitronates were reduced with hydrogen in the presence of Adam's catalyst to afford 3,3-disubstituted pyrrolidines which were isolated in good yield as their N-p-toluenesulfonamides 17. Cycloadditions of (E)-2-nitrostyrene with ethyl (E)- and (Z)-1-propenyl ethers provided for the stereoselective synthesis of cis- and trans-3-phenyl-4-methyl-N-(p-tolylsulfonyl)pyrrolidine. Similarly, trans-3,4-diphenyl-N-(p-tolylsulfonyl)pyrrolidine was prepared from (E)-2-nitrostyrene and ethyl (E)-2-styryl ether.

Original languageEnglish (US)
Pages (from-to)3857-3868
Number of pages12
JournalJournal of Organic Chemistry
Volume58
Issue number15
DOIs
StatePublished - Jan 1 1993

ASJC Scopus subject areas

  • Organic Chemistry

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