New chiral ferrocenyloxazolines: The first planar chiral triferrocenylmethane derivative and its use in asymmetric catalysis

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Original languageEnglish
Pages (from-to)2047-2052
Number of pages6
JournalJournal of Organometallic Chemistry
Volume694
Issue number13
Publication statusPublished - 10 Feb 2009

Abstract

New planar chiral enantiopure ferrocenyloxazolines have been prepared including ferrocenyldiphenylmethanol, diferrocenylphenylmethanol and triferrocenylmethanol derivatives (S,pR)-10 - (S,pR)-12, the latter being the first chiral triferrocenylmethanol derivative. The ferrocenyldiphenylmethanol derivative (S,pR)-10 has been crystallographically characterized. Asymmetric ethylation of some arylaldehydes using diethylzinc in the presence of the planar chiral triferrocenylmethanol derivative (S,pR)-12 afforded good yields and ees, which were higher than those obtained with related ferrocenyloxazolines.

Keywords

    Asymmetric catalysis, Chirality, Ferrocene ligands, Oxazolin, Triferrocenylmethanol

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New chiral ferrocenyloxazolines: The first planar chiral triferrocenylmethane derivative and its use in asymmetric catalysis. / Garabatos-Perera, José Ramon; Butenschön, Holger.
In: Journal of Organometallic Chemistry, Vol. 694, No. 13, 10.02.2009, p. 2047-2052.

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title = "New chiral ferrocenyloxazolines: The first planar chiral triferrocenylmethane derivative and its use in asymmetric catalysis",
abstract = "New planar chiral enantiopure ferrocenyloxazolines have been prepared including ferrocenyldiphenylmethanol, diferrocenylphenylmethanol and triferrocenylmethanol derivatives (S,pR)-10 - (S,pR)-12, the latter being the first chiral triferrocenylmethanol derivative. The ferrocenyldiphenylmethanol derivative (S,pR)-10 has been crystallographically characterized. Asymmetric ethylation of some arylaldehydes using diethylzinc in the presence of the planar chiral triferrocenylmethanol derivative (S,pR)-12 afforded good yields and ees, which were higher than those obtained with related ferrocenyloxazolines.",
keywords = "Asymmetric catalysis, Chirality, Ferrocene ligands, Oxazolin, Triferrocenylmethanol",
author = "Garabatos-Perera, {Jos{\'e} Ramon} and Holger Butensch{\"o}n",
note = "Funding information: We thank the Deutsche Forschungsgemeinschaft for generous support of our research. We are grateful to Octel Deutschland GmbH and to the Max-Planck-Institut f{\"u}r Kohlenforschung for donations of ferrocene.",
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TY - JOUR

T1 - New chiral ferrocenyloxazolines

T2 - The first planar chiral triferrocenylmethane derivative and its use in asymmetric catalysis

AU - Garabatos-Perera, José Ramon

AU - Butenschön, Holger

N1 - Funding information: We thank the Deutsche Forschungsgemeinschaft for generous support of our research. We are grateful to Octel Deutschland GmbH and to the Max-Planck-Institut für Kohlenforschung for donations of ferrocene.

PY - 2009/2/10

Y1 - 2009/2/10

N2 - New planar chiral enantiopure ferrocenyloxazolines have been prepared including ferrocenyldiphenylmethanol, diferrocenylphenylmethanol and triferrocenylmethanol derivatives (S,pR)-10 - (S,pR)-12, the latter being the first chiral triferrocenylmethanol derivative. The ferrocenyldiphenylmethanol derivative (S,pR)-10 has been crystallographically characterized. Asymmetric ethylation of some arylaldehydes using diethylzinc in the presence of the planar chiral triferrocenylmethanol derivative (S,pR)-12 afforded good yields and ees, which were higher than those obtained with related ferrocenyloxazolines.

AB - New planar chiral enantiopure ferrocenyloxazolines have been prepared including ferrocenyldiphenylmethanol, diferrocenylphenylmethanol and triferrocenylmethanol derivatives (S,pR)-10 - (S,pR)-12, the latter being the first chiral triferrocenylmethanol derivative. The ferrocenyldiphenylmethanol derivative (S,pR)-10 has been crystallographically characterized. Asymmetric ethylation of some arylaldehydes using diethylzinc in the presence of the planar chiral triferrocenylmethanol derivative (S,pR)-12 afforded good yields and ees, which were higher than those obtained with related ferrocenyloxazolines.

KW - Asymmetric catalysis

KW - Chirality

KW - Ferrocene ligands

KW - Oxazolin

KW - Triferrocenylmethanol

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U2 - 10.1016/j.jorganchem.2009.01.057

DO - 10.1016/j.jorganchem.2009.01.057

M3 - Article

AN - SCOPUS:65149094054

VL - 694

SP - 2047

EP - 2052

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

SN - 0022-328X

IS - 13

ER -