Alkoxide-induced ring opening of bicyclic 2-vinylcyclobutanones: A convenient synthesis of 2-vinyl-substituted 3-cycloalkene-1-carboxylic acid esters

The fused 2-vinyl or 2-phenyl substituted cyclobutanones 4 undergo stereoselective ring openings by the action of alkoxide ions (t-BuO(-) or MeO(-)) to produce novel vicinally disubstituted cycloalkene derivatives 5 and 6 in moderate to high yields. The ring cleavage usually occurs with complete reg...

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Published inBeilstein journal of organic chemistry Vol. 8; no. 1; pp. 650 - 657
Main Authors Ji, Xiufang, Li, Zhiming, Wang, Quanrui, Goeke, Andreas
Format Journal Article
LanguageEnglish
Published Germany Beilstein-Institut 26.04.2012
Subjects
alkoxide
Chemistry
cyclobutanones
esters
Full Research Paper
fused ring systems
ring opening
ring opening
cyclobutanones
esters
fused ring systems
alkoxide
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Summary:The fused 2-vinyl or 2-phenyl substituted cyclobutanones 4 undergo stereoselective ring openings by the action of alkoxide ions (t-BuO(-) or MeO(-)) to produce novel vicinally disubstituted cycloalkene derivatives 5 and 6 in moderate to high yields. The ring cleavage usually occurs with complete regioselectivity. The accessibility of γ,δ-unsaturated ester or acid derivatives makes this transformation a good supplementary method for the well-established Johnson-Claisen rearrangement.
Bibliography:ObjectType-Article-1
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ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.8.72