Synthesis of enantiomerically pure bicycle[4.2.0]octanes by Cu-catalyzed [2+2] photocycloaddition and enantiotopos-differentiating ring opening

Ingbert Braun; Florian Rudroff; Marko D. Mihovilovic; Thorsten Bach

doi:10.1002/anie.200600946

Synthesis of enantiomerically pure bicycle[4.2.0]octanes by Cu-catalyzed [2+2] photocycloaddition and enantiotopos-differentiating ring opening

Ingbert Braun, Florian Rudroff, Marko D. Mihovilovic, Thorsten Bach

Chair of Organic Chemistry 1

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

33 Scopus citations

Abstract

(Chemical Equation Presented) Fooling Mother Nature: When the bicyclo[4.2.0]octanes A are bridged as in precursors B (Z = CO), the otherwise impossible [2+2] photocycloaddition reaction of 1,7-dienes is possible with substrates such as C. A subsequent Baeyer-Villiger oxidation serves to desymmetrize substrates B and establishes a general approach to enantiomerically pure products A.

Original language	English
Pages (from-to)	5541-5543
Number of pages	3
Journal	Angewandte Chemie International Edition in English
Volume	45
Issue number	33
DOIs	https://doi.org/10.1002/anie.200600946
State	Published - 18 Aug 2006

Keywords

Asymmetric synthesis
Cycloaddition
Enantioselectivity
Lactones
Oxidation

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10.1002/anie.200600946

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title = "Synthesis of enantiomerically pure bicycle[4.2.0]octanes by Cu-catalyzed [2+2] photocycloaddition and enantiotopos-differentiating ring opening",

abstract = "(Chemical Equation Presented) Fooling Mother Nature: When the bicyclo[4.2.0]octanes A are bridged as in precursors B (Z = CO), the otherwise impossible [2+2] photocycloaddition reaction of 1,7-dienes is possible with substrates such as C. A subsequent Baeyer-Villiger oxidation serves to desymmetrize substrates B and establishes a general approach to enantiomerically pure products A.",

keywords = "Asymmetric synthesis, Cycloaddition, Enantioselectivity, Lactones, Oxidation",

author = "Ingbert Braun and Florian Rudroff and Mihovilovic, {Marko D.} and Thorsten Bach",

year = "2006",

month = aug,

day = "18",

doi = "10.1002/anie.200600946",

language = "English",

volume = "45",

pages = "5541--5543",

journal = "Angewandte Chemie International Edition in English",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "33",

}

Synthesis of enantiomerically pure bicycle[4.2.0]octanes by Cu-catalyzed [2+2] photocycloaddition and enantiotopos-differentiating ring opening. / Braun, Ingbert; Rudroff, Florian; Mihovilovic, Marko D. et al.
In: Angewandte Chemie International Edition in English, Vol. 45, No. 33, 18.08.2006, p. 5541-5543.

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

TY - JOUR

T1 - Synthesis of enantiomerically pure bicycle[4.2.0]octanes by Cu-catalyzed [2+2] photocycloaddition and enantiotopos-differentiating ring opening

AU - Braun, Ingbert

AU - Rudroff, Florian

AU - Mihovilovic, Marko D.

AU - Bach, Thorsten

PY - 2006/8/18

Y1 - 2006/8/18

N2 - (Chemical Equation Presented) Fooling Mother Nature: When the bicyclo[4.2.0]octanes A are bridged as in precursors B (Z = CO), the otherwise impossible [2+2] photocycloaddition reaction of 1,7-dienes is possible with substrates such as C. A subsequent Baeyer-Villiger oxidation serves to desymmetrize substrates B and establishes a general approach to enantiomerically pure products A.

AB - (Chemical Equation Presented) Fooling Mother Nature: When the bicyclo[4.2.0]octanes A are bridged as in precursors B (Z = CO), the otherwise impossible [2+2] photocycloaddition reaction of 1,7-dienes is possible with substrates such as C. A subsequent Baeyer-Villiger oxidation serves to desymmetrize substrates B and establishes a general approach to enantiomerically pure products A.

KW - Asymmetric synthesis

KW - Cycloaddition

KW - Enantioselectivity

KW - Lactones

KW - Oxidation

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JO - Angewandte Chemie International Edition in English

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ER -

Synthesis of enantiomerically pure bicycle[4.2.0]octanes by Cu-catalyzed [2+2] photocycloaddition and enantiotopos-differentiating ring opening

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