Design, synthesis, and application of a C2 symmetric chiral ligand for enantioselective conjugate addition of organolithium to α,β-unsaturated aldimine

Mitsuru Shindo, Kenji Koga, Kiyoshi Tomioka

Research output: Contribution to journalArticle

102 Citations (Scopus)

Abstract

A C2 symmetric chiral diether ligand, (1R,2R)-1,2-dimethoxy-1,2- diphenylethane, was designed and synthesized on the basis of the concept of an asymmetric oxygen atom. Mediated by the chiral diether, high enantioselectivities were achieved in conjugate addition of organolithiums to naphthaldehyde imine and cyclic and acyclic α,β-unsaturated aldimines. The absolute configuration of the product is predictable by the model.

Original languageEnglish
Pages (from-to)9351-9357
Number of pages7
JournalJournal of Organic Chemistry
Volume63
Issue number25
DOIs
Publication statusPublished - Dec 11 1998
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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