Synthesis of vinylcyclopropanes from epoxides

Ring-opening of epoxides 1 by heteroatom-substituted allyl anions 2 occurs with high regioselectivity. In situ tosylation of the resulting alkoxides 3 or tosylation of the corresponding alcohols 4 yields 4-pentenyl tosylates 5. Anion generation by deprotonation or desilylation gives vinylcyclopropan...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 56; no. 2; pp. 717 - 723
Main Authors Schaumann, Ernst, Kirschning, Andreas, Narjes, Frank
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.01.1991
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Exact sciences and technology
Organic chemistry
Physical Sciences
Science & Technology
ORGANIC-SYNTHESIS
1,3-DIENES
OXIRANES
AMBIENT-TEMPERATURE
SUBSTITUTED VINYLCYCLOPROPANES
GENERATION
VINYL-CYCLOPROPANES
ELECTROPHILES
STEREOSELECTIVE SYNTHESIS
CYCLO-ADDITION
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Summary:Ring-opening of epoxides 1 by heteroatom-substituted allyl anions 2 occurs with high regioselectivity. In situ tosylation of the resulting alkoxides 3 or tosylation of the corresponding alcohols 4 yields 4-pentenyl tosylates 5. Anion generation by deprotonation or desilylation gives vinylcyclopropanes 9 by an S(Ni) process. The approach allows annulation of vinylcyclopropanes onto existing five- and six-membered rings and synthesis of vinylcyclopropanes with functionality on the olefin.
Bibliography:ark:/67375/TPS-86RH5TW1-Q
istex:4DB8BB3EC0D3FC1743AC0AF422FE8DB0E2593771
ISSN:0022-3263
1520-6904
DOI:10.1021/jo00002a043