Palladium-Catalyzed Addition of Nitrogen Pronucleophiles to Alkylidenecyclopropanes

The inter- and intramolecular additions of cyclic amides (nitrogen pronucleophiles) to methylenecyclopropanes proceeded smoothly in the presence of catalytic amounts of Pd(PPh3)4, affording the corresponding hydroamination products in good to high yields with high regioselectivities. The ring openin...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 70; no. 15; pp. 5932 - 5937
Main Authors Siriwardana, Amal I, Kamada, Michiru, Nakamura, Itaru, Yamamoto, Yoshinori
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 22.07.2005
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
ALKYLIDENE CYCLOPROPANES
HYDROCARBONATION
METHYLENECYCLOPROPANES
COMPLEXES
CARBOPALLADATION
CODIMERIZATION
BICYCLOPROPYLIDENE
CAPTURE
Catalytic reaction
Transition element complexes
Cyclopropane derivatives
Regioselectivity
Nitrogen heterocycle
Lactam
Lactone
Palladium complex
Transition metal Complexes
Oxygen heterocycle
Ring cleavage
Cyclic compound
Carboxamide
Platinoid Complexes
Ethylenic compound
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Summary:The inter- and intramolecular additions of cyclic amides (nitrogen pronucleophiles) to methylenecyclopropanes proceeded smoothly in the presence of catalytic amounts of Pd(PPh3)4, affording the corresponding hydroamination products in good to high yields with high regioselectivities. The ring opening of methylenecyclopropanes occurred at the distal position of the cyclopropane ring.
Bibliography:istex:E600742A5AB3B81BEDD8DB9FFB057DA92F280019
ark:/67375/TPS-F64QFMBW-3
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo050700s