Lewis acid promoted hetero [2 + 2] cycloaddition reactions of aldehydes with 10-propynyl-9(10h)-acridone. A highly stereoselective synthesis of acrylic acid derivatives and 1,3-dienes using an electron deficient variant of ynamine

Richard P. Hsung, Craig A. Zificsak, Lin Li Wei, Christopher J. Douglas, Hui Xiong, Jason A. Mulder

Research output: Contribution to journalArticle

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Abstract

(matrix presented) Reactivities of 10-propynyl-9(10H)-acridone toward various aldehydes in BF3·Et20-promoted hetero [2 + 2] cycloaddition reactions are described here. This electron deficient variant of ynamine is more stable and easier to handle than most ynamines but possesses comparable reactivity. These reactions lead to a highly stereoselective synthesis of trisubstituted alkenes. A mechanistic model based on the stereochemical assignment is also described here. 10-Propynyl-9(10H)-acridone is also reactive toward α,β-unsaturated aldehydes and ketones. It provides hetero [2 + 2] products in reactions with α,β-unsaturated aldehydes but gives only the inverse demand [4 + 2] cycloadduct in a reaction with methyl vinyl ketone.

Original languageEnglish (US)
Pages (from-to)1237-1240
Number of pages4
JournalOrganic Letters
Volume1
Issue number8
DOIs
StatePublished - Oct 21 1999

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