Palladium-catalyzed [4 + 2] cycloaddition of o-(silylmethyl)benzyl esters with ketones: An equivalent to oxo-diels-alder reaction of o-xylylenes

Satoshi Ueno, Masakazu Ohtsubo, Ryoichi Kuwano

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Figure Presented. o-(Silylmethyl)benzyl carbonates reacted with various electron-deficient ketones in the presence of a palladium catalyst, affording the [4 + 2] cycloaddition products, isochromanes, in high yields. The palladium-catalyzed cycloaddition is equivalent to the oxo-Diels-Alder reaction of o-xylylene with ketones. The regioselectivities were extraordinarily affected by the structures of the o-xylylene precursors and ketones. The unusual regiochemistry may support two competitive reaction pathways in the catalytic reaction.

Original languageEnglish
Pages (from-to)4332-4334
Number of pages3
JournalOrganic Letters
Volume12
Issue number19
DOIs
Publication statusPublished - Oct 1 2010

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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