Preparation of P-heterocyclic phosphine boranes and optically active phosphine oxides via phosphonium salts

Réka Herbay, Péter Bagi, Elemér Fogassy, G. Keglevich

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The preparation of 3-phospholene boranes and optically active 3-phospholene oxides was elaborated via the corresponding cyclic chloro-phosphonium salt intermediates. The 3-phospholene oxides were reacted with oxalyl chloride to afford the corresponding chloro-phosphonium salts, which were reacted with LiBH4 to afford 3-phospholene boranes. This procedure is a practical one-pot method for the deoxygenation and borane complex formation of 3-phospholene oxides without using silanes. It was shown that 3- chlorophospholenium salts can be reacted with chiral alcohols to give diastereomerically enriched cyclic alkoxy-phospholium salt intermediates,whichwere converted to enantiomerically enriched 3-phospholene oxides by Arbuzov collapse.

Original languageEnglish
Pages (from-to)1656-1657
Number of pages2
JournalPhosphorus, Sulfur and Silicon and the Related Elements
Volume191
Issue number11-12
DOIs
Publication statusPublished - Dec 1 2016

Keywords

  • alkoxy-phosphonium salt
  • Borane complex
  • dynamic resolution
  • phospholene oxide
  • phosphonium salt

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Inorganic Chemistry

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