Synthesis of Highly Enantioenriched All-Carbon Quaternary Centers: Conjugate Additions of Chiral Organolithium Nucleophiles to α,α- Dinitrile β,β-Disubstituted Olefins

Doo Ok Jang, Dwight D. Kim, Do Kyu Pyun, Peter Beak

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

(Equation presented) Highly enantioenriched quaternary centers are obtained by the reaction of chiral lithiated intermediates complexed to (-)-sparteine with tetrasubstituted, α,α-dinitrile activated olefins. Lithiated N-Boc-N-Aryl benzylamine furnishes products with drs from 78:22 to 95:5, with ers exceeding 94:6. Lithiated N-Boc-N-Aryl allylamine reactants provide enecarbamate products with drs from 55:45 to 99:1, with ers ranging from 87:13 to 97:3.

Original languageEnglish
Pages (from-to)4155-4157
Number of pages3
JournalOrganic Letters
Volume5
Issue number22
DOIs
Publication statusPublished - 2003 Oct 30

    Fingerprint

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this