Ligand-Accelerated Asymmetric [1,2]-Stevens Rearrangment of Sulfur Ylides via Decomposition of Diazomalonates Catalyzed by Chiral Bisoxazoline/Copper Complex

The first example of catalytic asymmetric [1,2]‐Stevens rearrangement reaction of 1,3‐oxathiolanes with diazomalonates has been developed and up to 90% ee is achieved by the bisoxazoline 4e/copper(II) triflate [Cu(OTf)2] complex.

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 351; no. 3; pp. 308 - 312
Main Authors Qu, Jian-Ping, Xu, Zheng-Hu, Zhou, Jian, Cao, Chun-Li, Sun, Xiu-Li, Dai, Li-Xin, Tang, Yong
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 01.02.2009
WILEY‐VCH Verlag
Wiley
Subjects
asymmetric catalysis
bisoxazolines
Chemistry
Chemistry, Applied
Chemistry, Organic
Physical Sciences
Science & Technology
Stevens rearrangement
ylides
ylides
HIGHLY ENANTIOSELECTIVE SYNTHESIS
RING EXPANSION REACTION
Stevens rearrangement
BIS(OXAZOLINE) LIGANDS
DIAZO-COMPOUNDS
asymmetric catalysis
MICHAEL ADDITION
COPPER(II) COMPLEXES
DIELS-ALDER REACTION
bisoxazolines
3-COMPONENT REACTIONS
<2,3>-SIGMATROPIC REARRANGEMENT
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Summary:The first example of catalytic asymmetric [1,2]‐Stevens rearrangement reaction of 1,3‐oxathiolanes with diazomalonates has been developed and up to 90% ee is achieved by the bisoxazoline 4e/copper(II) triflate [Cu(OTf)2] complex.
Bibliography:istex:08E7238A56859002633554FE2A17715B7CC8885D
Chinese Academy of Sciences
ArticleID:ADSC200800536
Science and Technology Commission of Shanghai Municipality
Major State Basic Research Development Program - No. 2006CB806105
ark:/67375/WNG-SWH027S0-C
National Natural Science Foundation of China
ObjectType-Article-2
SourceType-Scholarly Journals-1
ObjectType-Feature-1
content type line 23
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200800536