Scandium trifluoromethanesulfonate-catalyzed cleavage of esters bearing a coordinative group at a vicinal position

被引：17

作者：

Kajiro, H

Mitamura, S

Mori, A

Hiyama, T

机构：

[1] Tokyo Inst Technol, Resources Utilizat Res Lab, Midori Ku, Yokohama, Kanagawa 2268503, Japan

[2] Nippon Steel Corp Ltd, Adv Technol Res Labs, Nakahara Ku, Kawasaki, Kanagawa 2110035, Japan

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1999年 / 72卷 / 07期

关键词：

D O I：

10.1246/bcsj.72.1553

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Scandium trifluoromethanesulfonate is found to be a Lewis acid catalyst for selective cleavage of esters containing a coordinative group adjacent to an ester moiety. The reaction proceeds under weak acidic conditions at room temperature; the catalyst can be recovered and reused. Even alpha-acyloxy ketones are deacetylated without racemization. Selective mono-deacetylation at C-10 of paclitaxel has been achieved.

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页码：1553 / 1560

页数：8

相关论文

共 40 条

[1] THE PHOTOELIMINATION OF N-NITROSO-N-ACETYL-ALPHA-AMINO ACIDS - A NEW SYNTHESIS OF 1,2,4-OXADIAZOLES [J].

CHOW, YL ;

POLO, JS .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1986, (05) :727-733

[2] CHIRAL ACYL ANION AND ENOLONIUM ION EQUIVALENTS - ASYMMETRIC-SYNTHESIS OF ALPHA-METHOXY-ALDEHYDES [J].

COLOMBO, L ;

GENNARI, C ;

SCOLASTICO, C ;

GUANTI, G ;

NARISANO, E .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (04) :1278-1283

[3] Lanthanide trifluoromethanesulfonate catalysed selective acylation of 10-deacetylbaccatin III [J].

Damen, EWP ;

Braamer, L ;

Scheeren, HW .

TETRAHEDRON LETTERS, 1998, 39 (33) :6081-6082

[4] Synthesis and Rhizopus oryzae mediated enantioselective hydrolysis of α-acetoxy aryl alkyl ketones [J].

Demir, AS ;

Hamamci, H ;

Tanyeli, C ;

Akhmedov, IM ;

Doganel, F .

TETRAHEDRON-ASYMMETRY, 1998, 9 (10) :1673-1677

[5] OXIDATION OF ARYL ALKYL KETONES TO ALPHA-ACYLOXY, ALPHA-(CAMPHORSULFONYLOXY), OR ALPHA-HYDROXY DERIVATIVES USING MANGANESE(III) ACETATE IN COMBINATION WITH CARBOXYLIC-ACIDS OR (1S)-(+)-10-CAMPHORSULFONIC ACID [J].

DEMIR, AS ;

CAMKERTEN, N ;

AKGUN, H ;

TANYELI, C ;

MAHASNEH, AS ;

WATT, DS .

SYNTHETIC COMMUNICATIONS, 1990, 20 (15) :2279-2289

[6] IODIDE DEALKYLATION OF BENZYL, PMB, PNB, AND T-BUTYL N-ACYL AMINO-ACID ESTERS VIA LITHIUM ION COORDINATION [J].

FISHER, JW ;

TRINKLE, KL .

TETRAHEDRON LETTERS, 1994, 35 (16) :2505-2508

[7]

GREENE TW, 1991, PROTECTIVE GROUPS OR, P10

[8] Ytterbium(III) triflate-catalyzed selective methanolysis of methoxyacetates: A new deprotective method [J].

Hanamoto, T ;

Sugimoto, Y ;

Yokoyama, Y ;

Inanaga, J .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (13) :4491-4492

[9] Scandium(III) perfluorooctanesulfonate [Sc(OPf)(3)]: A novel catalyst for the hetero Diels-Alder reaction of aldehydes with non-activated dienes [J].

Hanamoto, T ;

Sugimoto, Y ;

Jin, TZ ;

Inanaga, J .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1997, 70 (06) :1421-1426

[10]

INANAGA J, 1993, J CHEM SOC CHEM COMM, P1090

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