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Boron azaenolates of chiral oxazolines: synthesis of optically active formyl oxiranes

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
40
Issue
41
Identifiers
DOI: 10.1016/s0040-4039(99)01480-x
Keywords
  • Boron Azaenolates
  • Chiral Oxazolines
  • Chiral Chlorohydrins
  • Oxiranyl Oxazolines
  • Formyl Epoxides
Disciplines
  • Mathematics

Abstract

Abstract Boron azaenolates 2 and 8 from the optically active chloromethyloxazolines 1 and 7 have been found to couple with ketones in a highly diastereoselective fashion, which depends markedly upon the geometry (Z) of the azaenolates and the nature of the ligands which are present on the boron atom, in good accordance with semiempirical calculations (AM1).

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