New chiral catalysts: Synthesis and fragmentation pattern of C9-O-silanized cinchonidines

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1 Citation (Scopus)

Abstract

We synthesized C9-O-silyl ethers of cinchonidine and dihydrocinchonidine (1-8), seven of which have not been known before. The structures of the compounds were verified by ESI-ion-trap MS and 1H-NMR. Fragmentation of silyl ethers containing Si-phenyl bonds was studied for the first time. The compounds obtained will be utilized as chiral catalysts of certain asymmetric syntheses.

Original languageEnglish
Pages (from-to)281-289
Number of pages9
JournalReaction Kinetics and Catalysis Letters
Volume87
Issue number2
DOIs
Publication statusPublished - Apr 2006

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Ethers
ethers
fragmentation
catalysts
Catalysts
synthesis
Nuclear magnetic resonance
Ions
nuclear magnetic resonance
cinchonidine

Keywords

  • Chiral catalysts
  • Cinchonidine
  • Mass spectrometry
  • Silyl ethers

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Catalysis

Cite this

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title = "New chiral catalysts: Synthesis and fragmentation pattern of C9-O-silanized cinchonidines",
abstract = "We synthesized C9-O-silyl ethers of cinchonidine and dihydrocinchonidine (1-8), seven of which have not been known before. The structures of the compounds were verified by ESI-ion-trap MS and 1H-NMR. Fragmentation of silyl ethers containing Si-phenyl bonds was studied for the first time. The compounds obtained will be utilized as chiral catalysts of certain asymmetric syntheses.",
keywords = "Chiral catalysts, Cinchonidine, Mass spectrometry, Silyl ethers",
author = "I. Bucsi and S. Cser{\'e}nyi and K. Felf{\"o}ldi and M. Bart{\'o}k",
year = "2006",
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doi = "10.1007/s11144-006-0035-1",
language = "English",
volume = "87",
pages = "281--289",
journal = "Reaction Kinetics, Mechanisms and Catalysis",
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publisher = "Springer Netherlands",
number = "2",

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TY - JOUR

T1 - New chiral catalysts

T2 - Synthesis and fragmentation pattern of C9-O-silanized cinchonidines

AU - Bucsi, I.

AU - Cserényi, S.

AU - Felföldi, K.

AU - Bartók, M.

PY - 2006/4

Y1 - 2006/4

N2 - We synthesized C9-O-silyl ethers of cinchonidine and dihydrocinchonidine (1-8), seven of which have not been known before. The structures of the compounds were verified by ESI-ion-trap MS and 1H-NMR. Fragmentation of silyl ethers containing Si-phenyl bonds was studied for the first time. The compounds obtained will be utilized as chiral catalysts of certain asymmetric syntheses.

AB - We synthesized C9-O-silyl ethers of cinchonidine and dihydrocinchonidine (1-8), seven of which have not been known before. The structures of the compounds were verified by ESI-ion-trap MS and 1H-NMR. Fragmentation of silyl ethers containing Si-phenyl bonds was studied for the first time. The compounds obtained will be utilized as chiral catalysts of certain asymmetric syntheses.

KW - Chiral catalysts

KW - Cinchonidine

KW - Mass spectrometry

KW - Silyl ethers

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U2 - 10.1007/s11144-006-0035-1

DO - 10.1007/s11144-006-0035-1

M3 - Article

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VL - 87

SP - 281

EP - 289

JO - Reaction Kinetics, Mechanisms and Catalysis

JF - Reaction Kinetics, Mechanisms and Catalysis

SN - 1878-5190

IS - 2

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