Synthesis of novel chiral crown ethers derived from D-glucose and their application to an enantioselective Michael reaction

Péter Bakó, Zoltán Bajor, László Toke

Research output: Contribution to journalArticle

50 Citations (Scopus)

Abstract

New chiral monoaza-15-crown-5 derivatives anellated to methyl 4,6-di-O-butyl-α-D-glucopyranoside have been synthesized from 1 using the 4,6-O-benzylidene protecting group (removed by acetic acid) and 2,3-di-O-benzyl groups (removed by catalytic hydrogenolysis). The alkylation of the hydroxy groups in 1 and 5 with benzyl chloride and bis(2-chloroethyl) ether, respectively, were carried out in two-phase reactions using phase-transfer (PT) catalysts. These sugar-based crown ethers showed significant asymmetric induction as chiral PT catalysts in the Michael addition of 2-nitropropane to chalcone (90% ee). The substituent at the nitrogen atom of the crown ethers has a major influence on both the chemical yield and the enantioselectivity.

Original languageEnglish
Pages (from-to)3651-3655
Number of pages5
JournalJournal of the Chemical Society - Perkin Transactions 1
Issue number24
DOIs
Publication statusPublished - Dec 21 1999

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint Dive into the research topics of 'Synthesis of novel chiral crown ethers derived from D-glucose and their application to an enantioselective Michael reaction'. Together they form a unique fingerprint.

  • Cite this