@article{c4bb32f8d7fe49788058a61e6c5a06b9,
title = "A novel ketone synthesis by a palladium-catalyzed reaction of thiol esters and organozinc reagents",
abstract = "A variety of ketones have been prepared by a palladium-catalyzed reaction of ethanethiol esters with organozinc reagents. Various functional groups, including esters, ketones, aromatic halides and aldehydes, tolerate the reaction conditions. The reaction can also be applied to the synthesis of α-amino ketones using the corresponding L-α-amino thiol esters without racemization.",
author = "Hidetoshi Tokuyama and Satoshi Yokoshima and Tohru Yamashita and Tohru Fukuyama",
note = "Funding Information: Typical procedure: A dry, Ar-purged 50-mL flask containing a magnetic stirring bar is charged with N-Cbz-L-phenylalanine ethanethiol ester t7 (1.00 g, 2.91 mmol), PdC12(PPh3)2 (284 mg, 10 mol%), and toluene (10 mL). To the stirred mixture was added EtZnI (0.90 M in THF, 8.09 mL, 3.0 eq) 18 at room temperature and stirring was continued for 15 min. Diethyl ether (20 mL) was added and the suspension was passed through a pad of celite. The filtrate was washed with 1N HC1, sat. NaHCO3, brine, and dried over Na2SO 4. Filtration and concentration on rotary evaporator afforded a crude product. Purification on silica gel column chromatography (15-25% EtOAc in hexane gradient) gave the desired ketone (800 mg, 88% yield).19 Acknowledgment: This work was partially supported by Ministry of Education, Science Sports, and Culture, Japan (Grant-in-Aid for Encouragement of Young Scientists No. 09771897).",
year = "1998",
month = may,
day = "14",
doi = "10.1016/S0040-4039(98)00456-0",
language = "English",
volume = "39",
pages = "3189--3192",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Ltd.",
number = "20",
}