Catalytic Asymmetric Allylation of Hydrazono Esters in Aqueous Media by Using ZnF2-Chiral Diamine

Chiral homoallylic hydrazines are synthesized by catalytic asymmetric allylation of acylhydrazono esters with allyltrimethoxysilane by using a chiral Zn catalyst (see picture). The reactions proceed smoothly in aqueous media to give the allylated products in good to high yields and selectivities. Wa...

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Veröffentlicht in:Angewandte Chemie International Edition 2003-08, Vol.42 (33), p.3927-3930
Hauptverfasser: Hamada, Tomoaki, Manabe, Kei, Kobayashi, Shū
Format: Artikel
Sprache:eng
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Zusammenfassung:Chiral homoallylic hydrazines are synthesized by catalytic asymmetric allylation of acylhydrazono esters with allyltrimethoxysilane by using a chiral Zn catalyst (see picture). The reactions proceed smoothly in aqueous media to give the allylated products in good to high yields and selectivities. Water played an essential role in this reaction, and this is the first example of catalytic asymmetric allylation of CN bonds in aqueous media. R1=Me, Et; R2=p‐C6H4OMe, p‐C6H4OEt; R3=H, Me, Ph.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200351778