Synthesis of alkyl nitronates via Mitsunobu condensation

J. R. Falck, Jurong Yu

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Nitroalkanes bearing electron-withdrawing or unsaturated substituents at the α-carbon experience exclusive intra- and intermolecular 0-alkylation by alcohols under Mitsunobu condensation conditions furnishing good to excellent yields of alkyl nitronates; in contrast, 1-phenylsulphonyl-1-nitro-3-propanol affords mainly the corresponding cyclopropane.

Original languageEnglish (US)
Pages (from-to)6723-6726
Number of pages4
JournalTetrahedron Letters
Volume33
Issue number45
DOIs
StatePublished - Nov 3 1992

Fingerprint

Bearings (structural)
Alkylation
Condensation
Carbon
Alcohols
Electrons
cyclopropane
3-nitro-1-propanol

Keywords

  • 2-Isoxazoline-2-oxide
  • 5,6-dihydro-4H-oxazine-2-oxide
  • Mitsunobu
  • Nitronate
  • Nitronic ester

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of alkyl nitronates via Mitsunobu condensation. / Falck, J. R.; Yu, Jurong.

In: Tetrahedron Letters, Vol. 33, No. 45, 03.11.1992, p. 6723-6726.

Research output: Contribution to journalArticle

Falck, J. R. ; Yu, Jurong. / Synthesis of alkyl nitronates via Mitsunobu condensation. In: Tetrahedron Letters. 1992 ; Vol. 33, No. 45. pp. 6723-6726.
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