Stereocontrolled Catalysts of Reactions of Nitroalkanes

Abstract

The recognition of nitronate anions by cations derived from bicyclic amidine and guanidine bases has been studied by NMR, X-ray crystallography and semi-empirical molecular orbital theory. It has been clearly established that anions and cations form tightly-organised complexes by formation of pairs of parallel hydrogen bonds. A chiral bicyclic C2-symmetric guanidine has been synthesized in optically pure form from an alpha-amino acid starting material. It has been shown to complex carboxylic acids, and to catalyse the conjugate addition of nitroalkanes to electron-deficient alkenes with modest enantioselectivies. Nitroalkanes, Molecular recognition, Enantioselective catalysis.

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Document Details

Document Type
Technical Report
Publication Date
Jun 08, 1993
Accession Number
ADA269761

Entities

People

  • Anthony P. Davis
  • Brian A. Murray
  • Gladys D. Hosken
  • Maire A. Convery
  • Peter H. Boyle

Organizations

  • Trinity College Dublin

Tags

Communities of Interest

  • Air Platforms
  • Space

DTIC Thesaurus Topics

  • Amino Acids
  • Analogs
  • Carboxylic Acids
  • Catalysis
  • Chemical Synthesis
  • Chemistry
  • Crystal Structure
  • Crystallography
  • Hydrogen Bonds
  • Materials
  • Materials Science
  • Molecular Orbital Theory
  • Molecules
  • Organic Chemistry
  • Resonance
  • X Rays
  • X-Ray Crystallography

Fields of Study

  • Chemistry

Readers

  • Organic Chemistry

Technology Areas

  • Microelectronics
  • Space