Cycloaddition of enamines with alkynylphosphonates. A route to functionalized medium sized rings

Substituted seven and eight membered rings were formed from cyclopentanone and cyclo-hexanone via cycloadditions of pyrrolidine enamines with alkynyl phosphonates. This procedure provides straightforward access to functionalized medium sized rings that could be further manipulated in the synthesis o...

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Bibliographic Details
Published inTetrahedron letters Vol. 35; no. 21; pp. 3473 - 3476
Main Authors Ruder, Suzanne M., Norwood, Bradley K.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 23.05.1994
Elsevier
Subjects
Chemistry
Chemistry, Organic
Exact sciences and technology
Organic chemistry
Organometalloidal and organometallic compounds
P derivatives
Physical Sciences
Preparations and properties
Science & Technology
Five membered ring
Cycloaddition
Acetylenic compound
Nitrogen heterocycle
Enamine
Conjugated dienic compound
Phosphorus Organic compounds
Monocyclic compound
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Summary:Substituted seven and eight membered rings were formed from cyclopentanone and cyclo-hexanone via cycloadditions of pyrrolidine enamines with alkynyl phosphonates. This procedure provides straightforward access to functionalized medium sized rings that could be further manipulated in the synthesis of a number of natural products. Cyclic enamines and alkynyl phosphonates undergo reaction and thermal rearrangement to give ring expansion by two carbons, providing seven and eight membered rings.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)73213-8