Chiral biferrocene-based(oxazolines): Ligands for Cu(I)-catalyzed asymmetric cyclopropanations of ene-diazoacetates

Sung Gon Kim; Chang Woo Cho; Kyo Han Ahn

doi:10.1016/S0040-4020(99)00542-6

Chiral biferrocene-based(oxazolines): Ligands for Cu(I)-catalyzed asymmetric cyclopropanations of ene-diazoacetates

Sung Gon Kim
, Chang Woo Cho
, Kyo Han Ahn

Pohang University of Science and Technology

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

33 Scopus citations

Abstract

Chiral biferrocene-based bis(oxazoline) compounds, which have both planar and central chirality, are synthesized. The Cu(l)-complexes of the bis(oxazolinyl)biferrocenes were found to be conformationally flexible and have a wide bite angle (136^a) by NMR and molecular modeling studies. The complexes catalyzed the intramolecular cyclopropanation reaction of ene- diazoacetates, and low to moderate enantioselectivities and decreased reactivity were observed, compared to known malonate-derived bis(oxazoline) systems.

Original language	English
Pages (from-to)	10079-10086
Number of pages	8
Journal	Tetrahedron
Volume	55
Issue number	33
DOIs	https://doi.org/10.1016/S0040-4020(99)00542-6
State	Published - 13 Aug 1999

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title = "Chiral biferrocene-based(oxazolines): Ligands for Cu(I)-catalyzed asymmetric cyclopropanations of ene-diazoacetates",

abstract = "Chiral biferrocene-based bis(oxazoline) compounds, which have both planar and central chirality, are synthesized. The Cu(l)-complexes of the bis(oxazolinyl)biferrocenes were found to be conformationally flexible and have a wide bite angle (136a) by NMR and molecular modeling studies. The complexes catalyzed the intramolecular cyclopropanation reaction of ene- diazoacetates, and low to moderate enantioselectivities and decreased reactivity were observed, compared to known malonate-derived bis(oxazoline) systems.",

author = "Kim, \{Sung Gon\} and Cho, \{Chang Woo\} and Ahn, \{Kyo Han\}",

year = "1999",

month = aug,

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doi = "10.1016/S0040-4020(99)00542-6",

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pages = "10079--10086",

journal = "Tetrahedron",

issn = "0040-4020",

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T1 - Chiral biferrocene-based(oxazolines)

T2 - Ligands for Cu(I)-catalyzed asymmetric cyclopropanations of ene-diazoacetates

AU - Kim, Sung Gon

AU - Cho, Chang Woo

AU - Ahn, Kyo Han

PY - 1999/8/13

Y1 - 1999/8/13

N2 - Chiral biferrocene-based bis(oxazoline) compounds, which have both planar and central chirality, are synthesized. The Cu(l)-complexes of the bis(oxazolinyl)biferrocenes were found to be conformationally flexible and have a wide bite angle (136a) by NMR and molecular modeling studies. The complexes catalyzed the intramolecular cyclopropanation reaction of ene- diazoacetates, and low to moderate enantioselectivities and decreased reactivity were observed, compared to known malonate-derived bis(oxazoline) systems.

AB - Chiral biferrocene-based bis(oxazoline) compounds, which have both planar and central chirality, are synthesized. The Cu(l)-complexes of the bis(oxazolinyl)biferrocenes were found to be conformationally flexible and have a wide bite angle (136a) by NMR and molecular modeling studies. The complexes catalyzed the intramolecular cyclopropanation reaction of ene- diazoacetates, and low to moderate enantioselectivities and decreased reactivity were observed, compared to known malonate-derived bis(oxazoline) systems.

UR - https://www.scopus.com/pages/publications/0033551816

U2 - 10.1016/S0040-4020(99)00542-6

DO - 10.1016/S0040-4020(99)00542-6

M3 - Article

AN - SCOPUS:0033551816

SN - 0040-4020

VL - 55

SP - 10079

EP - 10086

JO - Tetrahedron

JF - Tetrahedron

IS - 33

ER -

Chiral biferrocene-based(oxazolines): Ligands for Cu(I)-catalyzed asymmetric cyclopropanations of ene-diazoacetates

Abstract

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