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
- ,
- ,
- 巻
- 64
- 号
- 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
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- DOI : 10.1021/jo9903398
- ISSN : 0022-3263
- CiNii Articles ID : 80011213982
- PubMed ID : 11674568
- Web of Science ID : WOS:000081136200049