Carbolithiation for the generation of cyclooctadienyl anions and tandem electrocyclization/alkylation to functionalized cis-bicyclo[3.3.0]octenes.

Carbolithiation for the generation of cyclooctadienyl anions and tandem electrocyclization/alkylation to functionalized cis-bicyclo[3.3.0]octenes. Research Abstract Details 

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Carbolithiation for the generation of cyclooctadienyl anions and tandem electrocyclization/alkylation to functionalized cis-bicyclo[3.3.0]octenes. Abstract Text:

David R Williams,Jonathan T Reeves,

A powerful cascade reaction process for the construction of functionalized cis-bicyclo[3.3.0]octenes has been developed. Carbolithiation of 3-methylene-1,4-cyclooctadiene with 1 degrees , 2 degrees , or 3 degrees alkyllithium reagents leads to cyclooctadienyl anions, which undergo disrotatory electrocyclization and subsequent trapping with carbon, oxygen, sulfur, or silicon electrophiles to provide functionalized cis-bicyclo[3.3.0]octenes. Transmetalation of the allyllithium intermediates allowed access to the cuprate manifold of reactivity. The rapid construction of a linear triquinane using this methodology demonstrates the potential for synthetic applications.

Carbolithiation for the generation of cyclooctadienyl anions and tandem electrocyclization/alkylation to functionalized cis-bicyclo[3.3.0]octenes. Publishing Authors By Initials

DR Williams,JT Reeves,

For similar organic chemicals: organometallic compounds research abstracts see: organic chemicals: organometallic compounds research

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Carbolithiation for the generation of cyclooctadienyl anions and tandem electrocyclization/alkylation to functionalized cis-bicyclo[3.3.0]octenes. Journal Published:

PUBLICATION TYPE: Research Support, U.S. Gov't,

Journal: Journal of the American Chemical Society

VOLUME: 126

Page Numbers: 3434-5

Journal Abbreviation: J. Am. Chem. Soc.

ISSN: 0002-7863

DAY: 24

MONTH: Mar

YEAR: 2004

Carbolithiation for the generation of cyclooctadienyl anions and tandem electrocyclization/alkylation to functionalized cis-bicyclo[3.3.0]octenes. Information

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LANGUAGE: eng

NlmUniqueID: 7503056

Carbolithiation for the generation of cyclooctadienyl anions and tandem electrocyclization/alkylation to functionalized cis-bicyclo[3.3.0]octenes. Keywords Mesh Terms:

KEYWORDS: Organometallic Compounds

MESH TERMS: chemistry

Chemical & Substance for Abstract: Carbolithiation for the generation of cyclooctadienyl anions and tandem electrocyclization/alkylation to functionalized cis-bicyclo[3.3.0]octenes. Information

Substance Name: Lithium

Registry Number: 7439-93-2

Grant and Affiliation Information for Carbolithiation for the generation of cyclooctadienyl anions and tandem electrocyclization/alkylation to functionalized cis-bicyclo[3.3.0]octenes.

AFFILIATION: Department of Chemistry, Indiana University, Bloomington, Indiana 47405-7102, USA. williamd@indiana.edu

Country: United States

AGENCY: United States NIGMS

GRANT: GM-41560

ACRONYM: GM

MEDLINETA: J Am Chem Soc

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