Chiral Lewis acid-catalyzed asymmetric Baylis-Hillman reactions

Kung Shuo Yang, Wei Der Lee, Jia Fu Pan, Kwunmin Chen

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Abstract

An effective chiral Lewis acid-catalyzed asymmetric Baylis-Hillman reaction is described. Good to high enantioselectivities were obtained using 3 mol % chiral catalyst. Novel camphor-derived dimerized ligands were prepared from the condensation of (+)-ketopinic acid with the corresponding diamines and hydrazine under acidic conditions. When α-naphthyl acrylate was used as a Michael acceptor, the reaction is complete within 20 min with high stereoselectivity and in reasonable chemical yields.

Original languageEnglish
Pages (from-to)915-919
Number of pages5
JournalJournal of Organic Chemistry
Volume68
Issue number3
DOIs
Publication statusPublished - 2003 Feb 7

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ASJC Scopus subject areas

  • Organic Chemistry

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