Organocatalytic asymmetric Friedel-Crafts alkylation/cyclization cascade reaction of 1-naphthols and α,β-unsaturated aldehydes: An enantioselective synthesis of chromanes and dihydrobenzopyranes

Liang Hong, Lei Wang, Wangsheng Sun, Kwok Yin Wong, Rui Wang

Research output: Journal article publicationJournal articleAcademic researchpeer-review

88 Citations (Scopus)

Abstract

(Chemical Equation Presented) An enantioselective Friedel-Crafts alkylation/cyclization cascade reaction of 1-naphthols and α,β- unsaturated aldehydes promoted by diphenylprolinol ether has been developed. The method affords one-pot access to chiral and synthetically useful chromanes and dihydrobenzopyranes in high yields and enantioselectivities from readily available compounds. In addition, the addition/cyclization products could be afterward transformed to various natural products and biologically active derivatives. On the basis of the experimental results and the observed absolute configurations of the products, a plausiblemechanismhasbeen proposed to explain the origin of the activation and the asymmetric induction.
Original languageEnglish
Pages (from-to)6881-6884
Number of pages4
JournalJournal of Organic Chemistry
Volume74
Issue number17
DOIs
Publication statusPublished - 4 Sep 2009

ASJC Scopus subject areas

  • Organic Chemistry

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