Nov, 2007
Stereoselective conjugate addition of lactams to nitroalkenes and formal total synthesis of indolizidine 167B
TETRAHEDRON
- ,
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- Volume
- 63
- Number
- 48
- First page
- 11856
- Last page
- 11861
- Language
- English
- Publishing type
- Research paper (scientific journal)
- DOI
- 10.1016/j.tet.2007.09.023
- Publisher
- PERGAMON-ELSEVIER SCIENCE LTD
Optically active 5-substituted pyrrolidin-2-ones underwent conjugate addition to nitroalkenes to give the corresponding adducts in a diastereoselective manner. The presence of 18-crown-6 was crucial to achieve good stereoselective addition. Addition of 6-substituted piperidin-2-ones also gave the corresponding adduct in a stereoselective manner. The adduct was readily converted into a bicyclic lactam through intramolecular nitroaldol reaction, and the formal synthesis of indolizidine 167B was achieved. (c) 2007 Elsevier Ltd. All rights reserved.
- Link information
-
- DOI
- https://doi.org/10.1016/j.tet.2007.09.023
- CiNii Articles
- http://ci.nii.ac.jp/naid/80018094765
- Web of Science
- https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000252094500009&DestApp=WOS_CPL
- URL
- http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=35348856841&origin=inward
- ID information
-
- DOI : 10.1016/j.tet.2007.09.023
- ISSN : 0040-4020
- CiNii Articles ID : 80018094765
- SCOPUS ID : 35348856841
- Web of Science ID : WOS:000252094500009