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PdCl2-Catalyzed Efficient Transformation of Propargylic Amines to (E)-α-Chloroalkylidene-β-lactams.
- Source :
-
Journal of Organic Chemistry . 4/1/2005, Vol. 70 Issue 7, p2588-2593. 6p. 4 Charts. - Publication Year :
- 2005
-
Abstract
- The PdCl2-catalyzed cyclocarbonylation reaction of propargylic amines with CuCl2 and benzoquinone afforded (E)-α-chloroalkylidene-β-lactams in moderate to good yields. The formation of the corresponding Z-isomers or five-membered products was not observed. The reaction of the readily available optically active prop argylic amines provides a convenient synthesis of the corresponding (E)-α-chloroalkylidene-β-lactams with high ee values. The structure and the stereochemistry of the products were established by the X-ray single-crystal diffraction study of (E)-6d and (E)-6e, which indicates that the stereoselectivity in this reaction is different from what was observed with propargylic alcohols. A rationale for this reaction was proposed. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 70
- Issue :
- 7
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 16643037
- Full Text :
- https://doi.org/10.1021/jo0480996