Pauson-Khand approach to chiral, diastereomerically pure group 4 ansa- metallocene complexes

Robert B. Grossman

doi:10.1016/S0040-4020(98)01099-0

Pauson-Khand approach to chiral, diastereomerically pure group 4 ansa- metallocene complexes

Robert B. Grossman

Chemistry

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

16 Scopus citations

Abstract

The C₂-symmetric bis(1,6-enynes) threo-1,10-diphenyl-5,6-divinyl-1,9- decadiyne and threo-9,10-divinyl-5,13-octadecadiyne undergo the intramolecular Pauson-Khand reaction regio- and stereoselectively to give C₂-symmetric bis(enones) with two bicyclo[3.3.0]octyl moieties joined at the C6 position. Experiments aimed at converting the bis(enones) into chiral, diastereopure ansa-bridged group 4 metallocene complexes are described.

Original language	English
Pages (from-to)	919-934
Number of pages	16
Journal	Tetrahedron
Volume	55
Issue number	4
DOIs	https://doi.org/10.1016/S0040-4020(98)01099-0
State	Published - Jan 22 1999

Bibliographical note

Funding Information:
Acknowledgements. The author thanks Dr. Michael Lloyd for solving the X-ray structure of 14a and the University of Kentucky for financial support of this work.

Keywords

Elimination reactions
Metalation
Pauson-Khand reaction
Polycyclic aliphatic compounds
Transition metals

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(98)01099-0

Cite this

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title = "Pauson-Khand approach to chiral, diastereomerically pure group 4 ansa- metallocene complexes",

abstract = "The C2-symmetric bis(1,6-enynes) threo-1,10-diphenyl-5,6-divinyl-1,9- decadiyne and threo-9,10-divinyl-5,13-octadecadiyne undergo the intramolecular Pauson-Khand reaction regio- and stereoselectively to give C2-symmetric bis(enones) with two bicyclo[3.3.0]octyl moieties joined at the C6 position. Experiments aimed at converting the bis(enones) into chiral, diastereopure ansa-bridged group 4 metallocene complexes are described.",

keywords = "Elimination reactions, Metalation, Pauson-Khand reaction, Polycyclic aliphatic compounds, Transition metals",

author = "Grossman, {Robert B.}",

note = "Funding Information: Acknowledgements. The author thanks Dr. Michael Lloyd for solving the X-ray structure of 14a and the University of Kentucky for financial support of this work.",

year = "1999",

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doi = "10.1016/S0040-4020(98)01099-0",

language = "English",

volume = "55",

pages = "919--934",

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T1 - Pauson-Khand approach to chiral, diastereomerically pure group 4 ansa- metallocene complexes

AU - Grossman, Robert B.

N1 - Funding Information: Acknowledgements. The author thanks Dr. Michael Lloyd for solving the X-ray structure of 14a and the University of Kentucky for financial support of this work.

PY - 1999/1/22

Y1 - 1999/1/22

N2 - The C2-symmetric bis(1,6-enynes) threo-1,10-diphenyl-5,6-divinyl-1,9- decadiyne and threo-9,10-divinyl-5,13-octadecadiyne undergo the intramolecular Pauson-Khand reaction regio- and stereoselectively to give C2-symmetric bis(enones) with two bicyclo[3.3.0]octyl moieties joined at the C6 position. Experiments aimed at converting the bis(enones) into chiral, diastereopure ansa-bridged group 4 metallocene complexes are described.

AB - The C2-symmetric bis(1,6-enynes) threo-1,10-diphenyl-5,6-divinyl-1,9- decadiyne and threo-9,10-divinyl-5,13-octadecadiyne undergo the intramolecular Pauson-Khand reaction regio- and stereoselectively to give C2-symmetric bis(enones) with two bicyclo[3.3.0]octyl moieties joined at the C6 position. Experiments aimed at converting the bis(enones) into chiral, diastereopure ansa-bridged group 4 metallocene complexes are described.

KW - Elimination reactions

KW - Metalation

KW - Pauson-Khand reaction

KW - Polycyclic aliphatic compounds

KW - Transition metals

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U2 - 10.1016/S0040-4020(98)01099-0

DO - 10.1016/S0040-4020(98)01099-0

M3 - Article

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SN - 0040-4020

VL - 55

SP - 919

EP - 934

JO - Tetrahedron

JF - Tetrahedron

IS - 4

ER -

Pauson-Khand approach to chiral, diastereomerically pure group 4 ansa- metallocene complexes

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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