Highly efficient catalytic asymmetric epoxidation of allylic alcohols by an oxovanadium-substituted polyoxometalate with a regenerative TADDOL-derived hydroperoxide

被引:43
作者
Adam, W
Alsters, PL
Neumann, R
Saha-Möller, CR
Seebach, D
Zhang, R [1 ]
机构
[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany
[2] Fine Chem Adv Synth & Catalysis, NL-6160 MD Geleen, Netherlands
[3] Weizmann Inst Sci, Dept Organ Chem, IL-76100 Rehovot, Israel
[4] ETH Honggerberg, HCI, Organ Chem Lab, CH-8093 Zurich, Switzerland
关键词
D O I
10.1021/ol027498p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The oxovanadium(IV) sandwich-type POM catalyzes the chemo-, regio-, and stereoselective epoxidation of allylic alcohols by chiral hydroperoxides with very high catalytic efficiency (up to 42 000 TON), a potentially valuable oxidation for the development of sustainable processes. By using the sterically demanding, TADDOL-derived hydroperoxide TADOOH as the chiral oxygen source, enantiomeric ratios (er) of up to 95:5 have been achieved.
引用
收藏
页码:725 / 728
页数:4
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