Papers

Nov, 2007

Stereoselective conjugate addition of lactams to nitroalkenes and formal total synthesis of indolizidine 167B

TETRAHEDRON
  • Akio Kamimura
  • ,
  • Yoshiaki Nagata
  • ,
  • Ayako Kadowaki
  • ,
  • Kosuke Uchida
  • ,
  • Hidemitsu Uno

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

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