Ring-opening iodo- and bromosilation of lactones for the formation of silyl haloalkanoates.
Ring-opening halosilation of lactones with two types of reagents, Et(3)SiH/MeI(PdCl(2)) (1a) and Et(3)SiH/AllylBr(PdCl(2)) (1b), was studied. Cyclic esters such as gamma-butyrolactones, delta-valerolactone, and 6-hexanolide reacted with 1 equiv of 1a,b to give triethylsilyl omega-iodo- and omega-bromoalkanoates in good yields. Reaction of an acyclic ester, methyl benzoate, with 1a afforded triethylsilyl benzoate. O-Silyl-protected amino acids could be obtained by amination of the halosilation products, triethylsilyl omega-bromoalkanoates.
Iwata
Arihiro
A
Department of Applied Chemistry,Graduate School of Engineering, Hiroshima University, Higashi-Hiroshima 739-8527, Japan.
Ohshita
Joji
J
Tang
Heqing
H
Kunai
Atsutaka
A
Yamamoto
Yasushi
Y
Matui
Chinami
C