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Studies on Pd(II)-Catalyzed Coupling-Cyclization of α-or β-Amino Allenes with Allylic Halides.
- Source :
-
Journal of Organic Chemistry . 7/25/2003, Vol. 68 Issue 15, p5943. 7p. 8 Diagrams, 4 Charts. - Publication Year :
- 2003
-
Abstract
- The palladium-catalyzed coupling-cyclization of α- or β-amino allenes with allylic halides leading to 3-allylic 2,5-dihydropyrroles and 1,2,3,6-tetrahydropyridines, respectively, was studied. The starting materials are easily available. The skeletons of both two classes of products were established by the X-ray diffraction studies of 7i and 9b. Through the study of the reaction of 2b with 3-chloro1-butene, 1-chloro-2-butene, and π-allyl palladium species and the stereochemical outcome of the coupling cyclization of (S)-2m and (R)-2n, it is believed that the current transformation most likely proceeded via a Pd(II)-catalyzed pathway, although a Pd(0) pathway cannot be completely excluded. [ABSTRACT FROM AUTHOR]
- Subjects :
- *ALLENE
*RING formation (Chemistry)
*CATALYSIS
*ALLYL halides
Subjects
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 68
- Issue :
- 15
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 10433152
- Full Text :
- https://doi.org/10.1021/jo0342469