Spontaneous resolution of a bis(eta(1)-methylcyclopentadienyl)zinc complex

S. Olsson, A. Lennartson

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

Resumé

Two crystalline complexes of bis(eta(1)-methylcyclopentadienyl)zinc, [Zn(C5H4Me)(2)(py)(2)] (1), where py is pyridine, and [Zn(C5H4Me)(2)(teeda)], 2, where teeda is N,N,N',N'-tetraethylethylenediamine have been isolated. The crystal structures of 1 and 2 are the first crystal structures for Zn(C5H4Me)(2) complexes reported in the literature; both structures display eta(1)-coordination of the methylcyclopentadienyl ring to zinc, and both compounds display chirogenic alpha-carbon atoms. While 1 forms racemic crystals, 2 undergoes spontaneous resolution and crystals of 2 are thus enantiomerically pure. H-1 NMR showed that Zn(C5H4Me)(2) is stereochemically labile in solution with only one signal for the Cp-protons. This fact opens up the possibility for total spontaneous resolution and absolute asymmetric synthesis. (C) 2011 Elsevier B.V. All rights reserved.
OriginalsprogEngelsk
TidsskriftInorganica Chimica Acta
Vol/bind377
Udgave nummer1
Sider (fra-til)181-184
Antal sider4
ISSN0020-1693
DOI
StatusUdgivet - 2011

Citer dette

Olsson, S. ; Lennartson, A. / Spontaneous resolution of a bis(eta(1)-methylcyclopentadienyl)zinc complex. I: Inorganica Chimica Acta. 2011 ; Bind 377, Nr. 1. s. 181-184.
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abstract = "Two crystalline complexes of bis(eta(1)-methylcyclopentadienyl)zinc, [Zn(C5H4Me)(2)(py)(2)] (1), where py is pyridine, and [Zn(C5H4Me)(2)(teeda)], 2, where teeda is N,N,N',N'-tetraethylethylenediamine have been isolated. The crystal structures of 1 and 2 are the first crystal structures for Zn(C5H4Me)(2) complexes reported in the literature; both structures display eta(1)-coordination of the methylcyclopentadienyl ring to zinc, and both compounds display chirogenic alpha-carbon atoms. While 1 forms racemic crystals, 2 undergoes spontaneous resolution and crystals of 2 are thus enantiomerically pure. H-1 NMR showed that Zn(C5H4Me)(2) is stereochemically labile in solution with only one signal for the Cp-protons. This fact opens up the possibility for total spontaneous resolution and absolute asymmetric synthesis. (C) 2011 Elsevier B.V. All rights reserved.",
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Spontaneous resolution of a bis(eta(1)-methylcyclopentadienyl)zinc complex. / Olsson, S.; Lennartson, A.

I: Inorganica Chimica Acta, Bind 377, Nr. 1, 2011, s. 181-184.

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

TY - JOUR

T1 - Spontaneous resolution of a bis(eta(1)-methylcyclopentadienyl)zinc complex

AU - Olsson, S.

AU - Lennartson, A.

PY - 2011

Y1 - 2011

N2 - Two crystalline complexes of bis(eta(1)-methylcyclopentadienyl)zinc, [Zn(C5H4Me)(2)(py)(2)] (1), where py is pyridine, and [Zn(C5H4Me)(2)(teeda)], 2, where teeda is N,N,N',N'-tetraethylethylenediamine have been isolated. The crystal structures of 1 and 2 are the first crystal structures for Zn(C5H4Me)(2) complexes reported in the literature; both structures display eta(1)-coordination of the methylcyclopentadienyl ring to zinc, and both compounds display chirogenic alpha-carbon atoms. While 1 forms racemic crystals, 2 undergoes spontaneous resolution and crystals of 2 are thus enantiomerically pure. H-1 NMR showed that Zn(C5H4Me)(2) is stereochemically labile in solution with only one signal for the Cp-protons. This fact opens up the possibility for total spontaneous resolution and absolute asymmetric synthesis. (C) 2011 Elsevier B.V. All rights reserved.

AB - Two crystalline complexes of bis(eta(1)-methylcyclopentadienyl)zinc, [Zn(C5H4Me)(2)(py)(2)] (1), where py is pyridine, and [Zn(C5H4Me)(2)(teeda)], 2, where teeda is N,N,N',N'-tetraethylethylenediamine have been isolated. The crystal structures of 1 and 2 are the first crystal structures for Zn(C5H4Me)(2) complexes reported in the literature; both structures display eta(1)-coordination of the methylcyclopentadienyl ring to zinc, and both compounds display chirogenic alpha-carbon atoms. While 1 forms racemic crystals, 2 undergoes spontaneous resolution and crystals of 2 are thus enantiomerically pure. H-1 NMR showed that Zn(C5H4Me)(2) is stereochemically labile in solution with only one signal for the Cp-protons. This fact opens up the possibility for total spontaneous resolution and absolute asymmetric synthesis. (C) 2011 Elsevier B.V. All rights reserved.

U2 - 10.1016/j.ica.2011.08.019

DO - 10.1016/j.ica.2011.08.019

M3 - Journal article

VL - 377

SP - 181

EP - 184

JO - Inorganica Chimica Acta

JF - Inorganica Chimica Acta

SN - 0020-1693

IS - 1

ER -