Chiral Lewis acid-catalyzed asymmetric Baylis-Hillman reactions

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

Research output: Contribution to journalArticle

113 Citations (Scopus)

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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hydrazine
Camphor
Stereoselectivity
Lewis Acids
Diamines
Enantioselectivity
Condensation
Ligands
Catalysts
ketopinic acid
acrylic acid

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Chiral Lewis acid-catalyzed asymmetric Baylis-Hillman reactions. / Yang, Kung Shuo; Lee, Wei Der; Pan, Jia Fu; Chen, Kwunmin.

In: Journal of Organic Chemistry, Vol. 68, No. 3, 07.02.2003, p. 915-919.

Research output: Contribution to journalArticle

Yang, Kung Shuo ; Lee, Wei Der ; Pan, Jia Fu ; Chen, Kwunmin. / Chiral Lewis acid-catalyzed asymmetric Baylis-Hillman reactions. In: Journal of Organic Chemistry. 2003 ; Vol. 68, No. 3. pp. 915-919.
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