Mass spektrometric studies on the formation of chiral N-sulphonylated oxazaborolidinones

Vesa Nevalainen (Corresponding Author), Timo Mansikka, Risto Kostiainen, Ilkka Simpura, Juha Kokkonen

Research output: Contribution to journalArticleScientificpeer-review

9 Citations (Scopus)

Abstract

The formation of N-tosyl-2-phenyl-1,3,2-oxazaborolidin-5-one 1 as a result of a condensation reaction between N-tosyl valine 2 and phenyl boronic acid was studied as a model of the formation of chiral oxazaborolidines used as Lewis acidic catalysts for various enantioselective syntheses. Intermediates of the formation of 1 along with those arising from further reactions (of 1) were investigated by electrospray ionization mass spectrometry (ESI-MS). Results of the study indicate that one phenyl boronic acid may react with one or two molecules of 2 and/or with one or two molecules of phenyl boronic acid. In addition, side-products implying dephenylation of 1 and self-condensation of phenyl boronic acid (formation of triphenylboroxine) were found.

Original languageEnglish
Pages (from-to)1-5
JournalTetrahedron: Asymmetry
Volume10
Issue number1
DOIs
Publication statusPublished - 1999
MoE publication typeA1 Journal article-refereed

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