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  • 标题:Planar Chiral [2.2]Paracyclophane-Based Bisoxazoline Ligands: Design, Synthesis, and Use in Cu-Catalyzed Inter- and Intramolecular Asymmetric O–H Insertion Reactions
  • 作者:Shinji Kitagaki ; Shunsuke Murata ; Kisaki Asaoka
  • 期刊名称:Chemical and Pharmaceutical Bulletin
  • 印刷版ISSN:0009-2363
  • 电子版ISSN:1347-5223
  • 出版年度:2018
  • 卷号:66
  • 期号:10
  • 页码:1006-1014
  • DOI:10.1248/cpb.c18-00519
  • 语种:English
  • 出版社:The Pharmaceutical Society of Japan
  • 摘要:Centrally chiral bisoxazolines connected directly to a planar chiral [2.2]paracyclophane backbone were synthesized and evaluated as asymmetric ligands in Cu-catalyzed intermolecular ethanolic O–H insertion reactions of α-diazo esters. The reactivities and enantioselectivities of Cu complexes of the synthesized bisoxazoline ligands were lower than those of ligands without central chirality. However, planar chiral [2.2]paracyclophane-based bisoxazoline ligands with an inserted benzene spacer that had a sterically demanding isopropyl substituent showed good enantioselectivities in inter- and intramolecular aromatic O–H insertion reactions, without the aid of central chirality.
  • 关键词:cyclophane;planar chirality;bisoxazoline;O–H insertion;copper
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