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Catalytic Asymmetric Allylation of Hydrazono Esters in Aqueous Media by Using ZnF 2 –Chiral Diamine
Author(s) -
Hamada Tomoaki,
Manabe Kei,
Kobayashi Shū
Publication year - 2003
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200351778
Subject(s) - aqueous medium , diamine , catalysis , aqueous solution , chemistry , polymer chemistry , organic chemistry
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 CN bonds in aqueous media. R 1 =Me, Et; R 2 = p ‐C 6 H 4 OMe, p ‐C 6 H 4 OEt; R 3 =H, Me, Ph.