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
Number of pages5
JournalTetrahedron: Asymmetry
Volume10
Issue number1
DOIs
Publication statusPublished - 1999
MoE publication typeA1 Journal article-refereed

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Boronic Acids
acids
Acids
condensation
Electrospray ionization
Molecules
Condensation reactions
Valine
Mass spectrometry
molecules
Condensation
mass spectroscopy
catalysts
ionization
Catalysts
oxazaborolidinone
synthesis
products

Cite this

Nevalainen, Vesa ; Mansikka, Timo ; Kostiainen, Risto ; Simpura, Ilkka ; Kokkonen, Juha. / Mass spektrometric studies on the formation of chiral N-sulphonylated oxazaborolidinones. In: Tetrahedron: Asymmetry. 1999 ; Vol. 10, No. 1. pp. 1-5.
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title = "Mass spektrometric studies on the formation of chiral N-sulphonylated oxazaborolidinones",
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.",
author = "Vesa Nevalainen and Timo Mansikka and Risto Kostiainen and Ilkka Simpura and Juha Kokkonen",
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Nevalainen, V, Mansikka, T, Kostiainen, R, Simpura, I & Kokkonen, J 1999, 'Mass spektrometric studies on the formation of chiral N-sulphonylated oxazaborolidinones', Tetrahedron: Asymmetry, vol. 10, no. 1, pp. 1-5. https://doi.org/10.1016/S0957-4166(98)00479-0

Mass spektrometric studies on the formation of chiral N-sulphonylated oxazaborolidinones. / Nevalainen, Vesa (Corresponding Author); Mansikka, Timo; Kostiainen, Risto; Simpura, Ilkka; Kokkonen, Juha.

In: Tetrahedron: Asymmetry, Vol. 10, No. 1, 1999, p. 1-5.

Research output: Contribution to journalArticleScientificpeer-review

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T1 - Mass spektrometric studies on the formation of chiral N-sulphonylated oxazaborolidinones

AU - Nevalainen, Vesa

AU - Mansikka, Timo

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AU - Kokkonen, Juha

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AB - 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.

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