Ring-Opening Iodo- and Bromosilation of Lactones for the Formation of Silyl Haloalkanoates
作者:Arihiro Iwata、Joji Ohshita、Heqing Tang、Atsutaka Kunai、Yasushi Yamamoto、Chinami Matui
DOI:10.1021/jo011153n
日期:2002.5.1
Ring-opening halosilation of lactones with two types of reagents, Et3SiH/MeI(PdCl2) (1a) and Et3SiH/AllylBr(PdCl2) (1b), was studied. Cyclic esters such as gamma-butyrolactones, delta-valerolactone, and 6-hexanolide reacted with 1 equiv of la,b to give triethylsilyl omega-iodo- and omega-bromoalkanoates in good yields. Reaction of an acyclic ester, methyl benzoate, with la afforded triethylsilyl benzoate. O-Silyl-protected amino acids could be obtained by amination of the halosilation products, triethylsilyl omega-bromoalkanoates.