S(N)2' reaction of organozinc reagents activated by catalytic tBu-P4 base in the presence of LiCl.
The tBu-P4 base was found to be an excellent catalyst for the activation of organozinc reagents. The base was used to promote the S(N)2' reaction of alpha,beta-unsaturated esters bearing a gamma-chloride in the reactions with various organozinc reagents in the presence of LiCl. The reactions proceeded in high yield with excellent chemo-and regioselectivity. The role of LiCl appears to be the activation of the gamma-chloride of the alpha,beta-unsaturated esters, which was confirmed by NMR spectroscopic study.
Kobayashi
Koji
K
Graduate School of Pharmaceutical Sciences, Tohoku University, Aramaki-aza Aoba 6-3, Aoba-ku, Sendai 980-8578, Japan.
Ueno
Masahiro
M
Naka
Hiroshi
H
Kondo
Yoshinori
Y
D002384:Catalysis; D018021:Lithium Chloride / Q000737:chemistry*; D009930:Organic Chemicals / Q000737:chemistry*; D010755:Organophosphates / Q000737:chemistry*; D015032:Zinc / Q000737:chemistry
D009930:Organic Chemicals; D010755:Organophosphates; C071068:tert-butyl phosphate; D018021:Lithium Chloride; D015032:Zinc