Concepedia

Atroposelectivity in the reactions of ortholithiated aromatic tertiary amides with aldehydes

Peter Bowles, Jonathan Clayden, Madeleine Helliwell, Catherine McCarthy, Matthew Tomkinson, Neil Westlund

Journal of the Chemical Society Perkin Transactions 1 · 1997 · 73 citations · 34 references

Concepts

Cross-coupling ReactionNovel OrganocatalystsEngineeringBiochemistryNatural SciencesOrtholithiated NOrganic ChemistryCatalysisStereoselective SynthesisChemistryDiastereoisomeric AtropisomersAsymmetric CatalysisSynthetic ChemistryEnantioselective SynthesisBiomolecular Engineering

Abstract

The products of the addition of ortholithiated N,N-dialkylnaphthamides to aldehydes are pairs of stable, diastereoisomeric atropisomers, formed with selectivities of up to 90∶10 in favour of the syn-atropisomer.

References

34

Dispersion corrections and crystal structure refinements

James A. Ibers, Walter C. Hamilton · Acta Crystallographica · 1964 · 1.3K citations · Full text

Crystal Structure, Engineering, Applied Physics +4

MITHRIL–an integrated direct-methods computer program

C. J. Gilmore · Journal of Applied Crystallography · 1984 · 706 citations

Engineering, Software Engineering, Computer-aided Design +17

Atroposelective Thermal Reactions of Axially Twisted Amides and Imides

Dennis P. Curran, Hongyan Qi, Steven J. Geib et al. · Journal of the American Chemical Society · 1994 · 237 citations

Materials Science, Cross-coupling Reaction, Engineering +9

Bestimmung des Aggregationsgrads lithiumorganischer Verbindungen durch Kryoskopie in Tetrahydrofuran

Walter Bauer, Dieter Seebàch · Helvetica Chimica Acta · 1984 · 197 citations

Food Chemistry, Enantioselective Synthesis, Engineering +10

Non‐Biaryl Atropisomers: New Classes of Chiral Reagents, Auxiliaries, and Ligands?

Jonathan Clayden · Angewandte Chemie International Edition in English · 1997 · 156 citations

Cross-coupling Reaction, Non‐biaryl Atropisomers, Atropisomeric Amides +12