A Simple, General, and Highly Chemoselective Acetylation of Alcohols Using Ethyl Acetate as the Acetyl Donor Catalyzed by a Tetranuclear Zinc Cluster

被引：37

作者：

Iwasaki, Takanori ^{[1
]}

Maegawa, Yusuke ^{[1
]}

Hayashi, Yukiko ^{[1
]}

Ohshima, Takashi ^{[1
]}

Mashima, Kazushi ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Engn Sci, Dept Chem, Osaka 5608531, Japan

来源：

SYNLETT | 2009年 / 10期

关键词：

zinc clusters; catalysis; acetylations; transesterifications; green chemistry; ASYMMETRIC ALDOL REACTION; SELECTIVE ACYLATION; METHIONINE AMINOPEPTIDASE; ORGANIC-REACTIONS; CARBOXYLIC-ACIDS; ALUMINA SURFACES; ENOL ESTERS; TRANSESTERIFICATION; AMINES; MILD;

D O I：

10.1055/s-0029-1217335

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the presence of a Zn-cluster catalyst, alcohols are efficiently converted to the corresponding acetate just by refluxing in EtOAc. The mild reaction conditions enabled the reactions of various functionalized alcohols to proceed in good to excellent yield. Moreover, even when a large excess of the acetyl donor is used, the hydroxyl groups are selectively acetylated in the presence of highly nucleophilic aliphatic amino groups, approaching chemoselectivity to that of enzymatic system.

引用

页码：1659 / 1663

页数：5

共 5 条

[1] Simple, general, and highly chemoselective acylation of alcohols catalyzed by tetranuclear zinc cluster
Ohshima, Takashi
Iwasaki, Takanori
Maegawa, Yusuke
Hayashi, Yukiko
Agura, Kazushi
Mashima, Kazushi
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 239
[2] Ethyl acetate as an acetyl surrogate for the iodine catalyzed acetylation of alcohols
Basumatary, Grace
Bez, Ghanashyam
TETRAHEDRON LETTERS, 2017, 58 (45) : 4312 - 4315
[3] Reformatsky Reagent Promoted Acetylation of Primary and Secondary Aliphatic Alcohols Using Ethyl Acetate as an Acetyl Donor
Fujihara, Rina
Nakata, Kenya
CHEMISTRYSELECT, 2019, 4 (01): : 75 - 77
[4] Enzyme-like chemoselective acylation of alcohols in the presence of amines catalyzed by a tetranuclear zinc cluster
Ohshima, Takashi
Iwasaki, Takanori
Maegawa, Yusuke
Yoshiyama, Asako
Mashima, Kazushi
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (10) : 2944 - 2945
[5] Chemoselective N-acetylation of primary aliphatic amines promoted by pivalic or acetic acid using ethyl acetate as an acetyl donor
Yoshida, Tomoki
Kawamura, Shimpei
Nakata, Kenya
TETRAHEDRON LETTERS, 2017, 58 (12) : 1181 - 1184

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