Synthesis, characterization and reactions of enantiomerically pure 'winged' spirane porphyrazines

Shun ichiro Hachiya; Andrew S. Cook; D. Bradley G. Williams; Antonio Garrido Montalban; Anthony G.M. Barrett; Brian M. Hoffman

doi:10.1016/S0040-4020(00)00607-4

Synthesis, characterization and reactions of enantiomerically pure 'winged' spirane porphyrazines

Shun ichiro Hachiya, Andrew S. Cook, D. Bradley G. Williams, Antonio Garrido Montalban, Anthony G.M. Barrett, Brian M. Hoffman

Chemistry

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

13 Scopus citations

Abstract

A series of enantiomerically pure porphyrazineoctaol derivatives have been prepared from L-(+)-dimethyl tartrate via conversion into the corresponding dispoke protected dihydroxymaleonitrile, Linstead macrocyclization and transmetallation. The derived chloromanganese(III) complexes catalyzed the epoxidation of styrene with sodium hypochlorite as the oxygen atom source but with modest enantioselectivities (<25%). (C) 2000 Elsevier Science Ltd. All rights reserved.

Original language	English (US)
Pages (from-to)	6565-6569
Number of pages	5
Journal	Tetrahedron
Volume	56
Issue number	35
DOIs	https://doi.org/10.1016/S0040-4020(00)00607-4
State	Published - Aug 25 2000

Keywords

Asymmetric induction
Complexes
Epoxidation
Porphyrins and analogs

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(00)00607-4

Cite this

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title = "Synthesis, characterization and reactions of enantiomerically pure 'winged' spirane porphyrazines",

abstract = "A series of enantiomerically pure porphyrazineoctaol derivatives have been prepared from L-(+)-dimethyl tartrate via conversion into the corresponding dispoke protected dihydroxymaleonitrile, Linstead macrocyclization and transmetallation. The derived chloromanganese(III) complexes catalyzed the epoxidation of styrene with sodium hypochlorite as the oxygen atom source but with modest enantioselectivities (<25%). (C) 2000 Elsevier Science Ltd. All rights reserved.",

keywords = "Asymmetric induction, Complexes, Epoxidation, Porphyrins and analogs",

author = "Hachiya, {Shun ichiro} and Cook, {Andrew S.} and Williams, {D. Bradley G.} and Montalban, {Antonio Garrido} and Barrett, {Anthony G.M.} and Hoffman, {Brian M.}",

note = "Funding Information: We thank the Glaxo Group Research Ltd. for the generous endowment (A. G. M. B.), the Wolfson Foundation for establishing the Wolfson Centre for Organic Chemistry in Medicinal Science at Imperial College, the Engineering and Physical Sciences Research Council, the National Science Foundation and NATO for generous support of our studies.",

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pages = "6565--6569",

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T1 - Synthesis, characterization and reactions of enantiomerically pure 'winged' spirane porphyrazines

AU - Hachiya, Shun ichiro

AU - Cook, Andrew S.

AU - Williams, D. Bradley G.

AU - Montalban, Antonio Garrido

AU - Barrett, Anthony G.M.

AU - Hoffman, Brian M.

N1 - Funding Information: We thank the Glaxo Group Research Ltd. for the generous endowment (A. G. M. B.), the Wolfson Foundation for establishing the Wolfson Centre for Organic Chemistry in Medicinal Science at Imperial College, the Engineering and Physical Sciences Research Council, the National Science Foundation and NATO for generous support of our studies.

PY - 2000/8/25

Y1 - 2000/8/25

N2 - A series of enantiomerically pure porphyrazineoctaol derivatives have been prepared from L-(+)-dimethyl tartrate via conversion into the corresponding dispoke protected dihydroxymaleonitrile, Linstead macrocyclization and transmetallation. The derived chloromanganese(III) complexes catalyzed the epoxidation of styrene with sodium hypochlorite as the oxygen atom source but with modest enantioselectivities (<25%). (C) 2000 Elsevier Science Ltd. All rights reserved.

AB - A series of enantiomerically pure porphyrazineoctaol derivatives have been prepared from L-(+)-dimethyl tartrate via conversion into the corresponding dispoke protected dihydroxymaleonitrile, Linstead macrocyclization and transmetallation. The derived chloromanganese(III) complexes catalyzed the epoxidation of styrene with sodium hypochlorite as the oxygen atom source but with modest enantioselectivities (<25%). (C) 2000 Elsevier Science Ltd. All rights reserved.

KW - Asymmetric induction

KW - Complexes

KW - Epoxidation

KW - Porphyrins and analogs

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DO - 10.1016/S0040-4020(00)00607-4

M3 - Article

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VL - 56

SP - 6565

EP - 6569

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 35

ER -

Synthesis, characterization and reactions of enantiomerically pure 'winged' spirane porphyrazines

Abstract

Keywords

ASJC Scopus subject areas

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