MISC

1999年6月

Diastereo- and enantioselective synthesis of beta-amino cyclic ethers via the intramolecular reaction of gamma-alkoxyallylstannane with imine

JOURNAL OF ORGANIC CHEMISTRY
  • JY Park
  • ,
  • Kadota, I
  • ,
  • Y Yamamoto

64
13
開始ページ
4901
終了ページ
4908
記述言語
英語
掲載種別
DOI
10.1021/jo9903398
出版者・発行元
AMER CHEMICAL SOC

The intramolecular Lewis acid mediated cyclization of gamma-alkoxyallylstannanes 1, 2, and 14, bearing a hydrazone group at the terminus of the carbon chain, afforded exclusively the corresponding trans beta-amino cyclic ethers 3a, 4a, and 15, respectively. The Lewis acid mediated cyclization of gamma-alkoxyallylstannane 5, having (R)-(+)-1-phenylethylamine as a chiral auxiliary, afforded exclusively traits beta-amino cyclic ether 6a with very high diastereomeric excess (de) in very high chemical yields. The asymmetric cyclization of gamma-alkoxyallylstannane with imine 7 in the presence of chiral titanium-BINOL complex 9, afforded predominantly cis beta-amino cyclic ether 8b with high enantiomeric excess tee). The chiral Lewis acid mediated cyclization of racemic compound 38 containing phenyl as a substituent afforded cis isomer 39 with very high enantiomeric excess (ee).

リンク情報
DOI
https://doi.org/10.1021/jo9903398
CiNii Articles
http://ci.nii.ac.jp/naid/80011213982
PubMed
https://www.ncbi.nlm.nih.gov/pubmed/11674568
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000081136200049&DestApp=WOS_CPL
ID情報
  • DOI : 10.1021/jo9903398
  • ISSN : 0022-3263
  • CiNii Articles ID : 80011213982
  • PubMed ID : 11674568
  • Web of Science ID : WOS:000081136200049

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