Catalytic asymmetric Tamura cycloadditions involving nitroalkenes

Francesco Manoni, Umar Farid, Cristina Trujillo, Stephen J. Connon*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

The first examples of asymmetric Tamura cycloaddition reactions involving singly activated alkenes are reported. Homophthalic anhydride reacts with α-methyl nitrosytrenes in the presence of an alkaloid-based catalyst to generate fused bicyclic aromatic ketone products with three new stereocentres (which are susceptible to subsequent equilibration) in 12-99% ee. An unusual equilibration process which occurs in methanolic medium in the absence of a recognisable base via proton transfer at the α-carbon of an ester was investigated experimentally and computationally.

Original languageEnglish
Pages (from-to)1463-1474
Number of pages12
JournalOrganic and Biomolecular Chemistry
Volume15
Issue number6
Early online date23 Jan 2017
DOIs
Publication statusPublished - 14 Feb 2017

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