Facile metal-assisted hydrolysis of a urethane

被引：7

作者：

Kelly, TR ^{[1
]}

Cavero, M ^{[1
]}

Zhao, Y ^{[1
]}

机构：

[1] Boston Coll, EF Merkert Chem Ctr, Chestnut Hill, MA 02467 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 24期

关键词：

D O I：

10.1021/ol016867z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Kinetic studies demonstrate that it is possible to achieve large rate enhancements (2 x 10(4)) for the hydrolysis of a urethane group by using metal-bound water or hydroxide as the nucleophile.

引用

页码：3895 / 3898

页数：4

共 17 条

[1] ESTERS OF CARBAMIC ACID [J].

ADAMS, P ;

BARON, FA .

CHEMICAL REVIEWS, 1965, 65 (05) :567-&

[2]

ALBERT A, 1984, DETERMINATION IONIZA, P31

[3] RECENT PERSPECTIVES CONCERNING THE MECHANISM OF H3O+-PROMOTED AND OH--PROMOTED AMIDE HYDROLYSIS [J].

BROWN, RS ;

BENNET, AJ ;

SLEBOCKATILK, H .

ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (11) :481-488

[4] DEVELOPING ARTIFICIAL HYDROLYTIC METALLOENZYMES BY A UNIFIED MECHANISTIC APPROACH [J].

CHIN, J .

ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (05) :145-152

[5] RATES OF HYDROLYSIS OF CARBAMATE AND CARBONATE ESTERS IN ALKALINE SOLUTION [J].

DITTERT, LW ;

HIGUCHI, T .

JOURNAL OF PHARMACEUTICAL SCIENCES, 1963, 52 (09) :852-&

[6] MODELS OF ZINC-CONTAINING PROTEASES - CATALYSIS OF COBALT(III)-MEDIATED AMIDE HYDROLYSIS BY A PENDANT CARBOXYLATE [J].

GROVES, JT ;

BARON, LA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) :5442-5448

[7]

Hegarty A. F., 1979, COMPREHENSIVE ORGANI, V2, P1067

[8]

HEYWANG G, 1983, KOHLENSAURE DERIVA E, V4, P1

[9] A rationally designed prototype of a molecular motor [J].

Kelly, TR ;

Silva, RA ;

De Silva, H ;

Jasmin, S ;

Zhao, YJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (29) :6935-6949

[10] Unidirectional rotary motion in a molecular system [J].

Kelly, TR ;

De Silva, H ;

Silva, RA .

NATURE, 1999, 401 (6749) :150-152

← 1 2 →