Ring-Opening Metathesis/Oxy-Cope Rearrangement:  A New Strategy for the Synthesis of Bicyclic Medium Ring-Containing Compounds

Ring-Opening Metathesis/Oxy-Cope Rearrangement:  A New Strategy for the Synthesis of Bicyclic Medium Ring-Containing Compounds

Ring-opening/ring-closing metathesis on cyclobutene-containing substrates with angular oxygen functionality provides a stereospecific introduction of 1,5-bis-dienes required for an anion-accelerated oxy-Cope rearrangement. The reaction sequence offers generally a stereocontrolled preparation of a va...

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Bibliographic Details
Published in:Journal of the American Chemical Society Vol. 125; no. 48; pp. 14901 - 14904
Main Authors: White, Brian H, Snapper, Marc L
Format: Journal Article
Language:English
Published: Washington, DC American Chemical Society 03-12-2003
Subjects:
Chemistry
Exact sciences and technology
Organic chemistry
Stereoselectivity
Cope rearrangement
Metathesis
Polycyclic compound
Stereospecificity
Experimental study
Oxygen heterocycle
Ring expansion
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Description
Summary:Ring-opening/ring-closing metathesis on cyclobutene-containing substrates with angular oxygen functionality provides a stereospecific introduction of 1,5-bis-dienes required for an anion-accelerated oxy-Cope rearrangement. The reaction sequence offers generally a stereocontrolled preparation of a variety of medium ring-containing bicyclic ring systems, while rearrangement to the bicyclo[7,3,0]dodecane (9-5) system leads to a mixture of olefin isomers.
Bibliography:ark:/67375/TPS-4R3T67NK-X
istex:6D1A7A05476F4D296C92FEA3FF3B0805F6200A81
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja037656n