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NHC-catalysed enantioselectiveintramolecular formal [4+2] cycloadditions using carboxylic acids as azolium enolate precursors

Research output: Contribution to journalArticlepeer-review

Author(s)

Nassilia Attaba, Andrew D. Smith

School/Research organisations

Abstract

An NHC-catalysed intramolecular formal [4 + 2] cycloaddition protocol using carboxylic acid starting materials containing a tethered enone is reported. Optimisation studies using a model substrate showed that the use of the Yamaguchi reagent (2,4,6-trichlorobenzoyl chloride) for in situ preparation of a mixed anhydride was necessary for effective catalysis, leading to highest product yield and stereoselectivity. Using this protocol, a range of dihydrobenzofurans were accessed in moderate to high yield, and with high to excellent diastereo- and enantioselectivity (up to > 95:5 dr and > 99:1 er). This methodology was extended to the synthesis of syn-dihydrochromenone and syn-dihydropyranone derivatives in moderate to high yield and with excellent diastereo- and enantioselectivity.
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Original languageEnglish
JournalTetrahedron
VolumeIn press
Early online date6 Dec 2019
DOIs
Publication statusE-pub ahead of print - 6 Dec 2019

    Research areas

  • NHC, Enantioselective catalysis, [4+2] cycloaddition, Carboxylic acid, Yamaguchi reagent

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