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

Vesa Nevalainen; Timo Mansikka; Risto Kostiainen; Ilkka Simpura; Juha Kokkonen

doi:10.1016/S0957-4166(98)00479-0

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

Vesa Nevalainen^*
, Timo Mansikka
, Risto Kostiainen
, Ilkka Simpura
, Juha Kokkonen

^*Corresponding author for this work

VTT Technical Research Centre of Finland

University of Helsinki

Research output: Contribution to journal › Article › Scientific › peer-review

10 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 language	English
Pages (from-to)	1-5
Journal	Tetrahedron: Asymmetry
Volume	10
Issue number	1
DOIs	https://doi.org/10.1016/S0957-4166(98)00479-0
Publication status	Published - 1999
MoE publication type	A1 Journal article-refereed

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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",

year = "1999",

doi = "10.1016/S0957-4166(98)00479-0",

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TY - JOUR

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

AU - Nevalainen, Vesa

AU - Mansikka, Timo

AU - Kostiainen, Risto

AU - Simpura, Ilkka

AU - Kokkonen, Juha

PY - 1999

Y1 - 1999

N2 - 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.

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.

U2 - 10.1016/S0957-4166(98)00479-0

DO - 10.1016/S0957-4166(98)00479-0

M3 - Article

SN - 0957-4166

VL - 10

SP - 1

EP - 5

JO - Tetrahedron: Asymmetry

JF - Tetrahedron: Asymmetry

IS - 1

ER -

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

Abstract

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