MISC

2010年12月

Studies on two different diastereoselective reaction pathways from a serinol derivative to 4-hydroxymethyl-2-oxazolidinones using 2-chloroethyl chloroformate and N,N '-disuccinimidyl carbonate

TETRAHEDRON-ASYMMETRY
  • Shigeo Sugiyama
  • ,
  • Keitaro Ishii

21
24
開始ページ
2904
終了ページ
2910
記述言語
英語
掲載種別
DOI
10.1016/j.tetasy.2010.11.022
出版者・発行元
PERGAMON-ELSEVIER SCIENCE LTD

Two reaction pathways and their diastereoselectivity-determining steps of the asymmetric desymmetrization of (R)-2-(alpha-methylbenzyl)amino-1,3-propanediol 1 with 2-chloroethyl chloroformate (CCF) and with N,N'-disuccinimidyl carbonate giving (4S,alpha R)-4-hydroxymethyl-3-alpha-methylbenzyl-2-oxazolidinones (4S)-3 and its (4R,alpha R)-diastereomer (4R)-3 were investigated. The reaction of serinol 1 and CCF to give the corresponding carbonates was not a diastereoselectivity-determining step. The carbonates gave (R)-5-(alpha-methylbenzyl)amino-1,3-dioxan-2-one 4 after addition of DBU, and an intramolecular acyl transfer of 4 was found to be a diastereoselectivity-determining step to give (4S)-3. Conversely, the reaction of serinol 1 and N,N'-disuccinimidyl carbonate afforded directly the opposite diastereomer (4R)-3 but not via the intermediate 4. Thus, their diastereoselectivities depended on the acylating reagent. (C) 2010 Elsevier Ltd. All rights reserved.


リンク情報
DOI
https://doi.org/10.1016/j.tetasy.2010.11.022
CiNii Articles
http://ci.nii.ac.jp/naid/80021638690
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000287295400003&DestApp=WOS_CPL
ID情報
  • DOI : 10.1016/j.tetasy.2010.11.022
  • ISSN : 0957-4166
  • CiNii Articles ID : 80021638690
  • Web of Science ID : WOS:000287295400003

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