An efficient protection of carbonyls and deprotection of acetals using decaborane

被引：45

作者：

Lee, SH ^{[1
]}

Lee, JH ^{[1
]}

Yoon, CM ^{[1
]}

机构：

[1] Korea Univ, Grad Sch Biotechnol, Seoul, South Korea

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 15期

关键词：

carbonyls; acetals; protection; decaborane; chemoselective;

D O I：

10.1016/S0040-4039(02)00387-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Carbonyls were efficiently converted to the corresponding dimethyl acetals at room temperature using trimethyl orthoformate and 1 mol% of decaborane under a nitrogen atmosphere. In turn. acetals ere deprotected to the corresponding carbonyls using 1 mol% of decaborane in aqueous THF chemoselectively. (C) 2002 Elsevier Science Ltd. All rights reserved.

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收藏

页码：2699 / 2703

页数：5

相关论文

共 28 条

[1] A one-pot synthesis of N-alkylaminobenzenes from nitroaromatics:: reduction followed by reductive amination using B10H14 [J].

Bae, JW ;

Cho, YJ ;

Lee, SH ;

Yoon, COM ;

Yoon, CM .

CHEMICAL COMMUNICATIONS, 2000, (19) :1857-1858

[2] Reduction of ketones to alcohols using a decaborane/pyrrolidine/cerium(III) chloride system in methanol [J].

Bae, JW ;

Lee, SH ;

Jung, YJ ;

Yoon, COM ;

Yoon, CM .

TETRAHEDRON LETTERS, 2001, 42 (11) :2137-2139

[3]

CAMPBELL, 1964, IN PRESS BORON CHEM, V1, P173

[4] Efficient acetalisation of aldehydes catalyzed by titanium tetrachloride in a basic medium [J].

Clerici, A ;

Pastori, N ;

Porta, O .

TETRAHEDRON, 1998, 54 (51) :15679-15690

[5] A simple chemoselective method for the deprotection of acetals and ketals using bismuth nitrate pentahydrate [J].

Eash, KJ ;

Pulia, MS ;

Wieland, LC ;

Mohan, RS .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (24) :8399-8401

[6] TIN(II) CHLORIDE DIHYDRATE - A MILD AND EFFICIENT REAGENT FOR CLEAVING ACETALS [J].

FORD, KL ;

ROSKAMP, EJ .

TETRAHEDRON LETTERS, 1992, 33 (09) :1135-1138

[7] Acetal and ketal deprotection using montmorillonite K10: The first synthesis of syn-4,8-dioxatricyclo[5.1.0.0(3,5)]-2,6-octanedione [J].

Gautier, ECL ;

Graham, AE ;

McKillop, A ;

Standen, SP ;

Taylor, RJK .

TETRAHEDRON LETTERS, 1997, 38 (11) :1881-1884

[8] LANTHANOIDS IN ORGANIC-SYNTHESIS .4. SELECTIVE KETALIZATION AND REDUCTION OF CARBONYL GROUPS [J].

GEMAL, AL ;

LUCHE, JL .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (23) :4187-4189

[9]

GREENE TW, 1991, PROTECTIVE GROUPS OR, P188

[10] THE ROLE OF CHEMISTRY IN THE DEVELOPMENT OF BORON NEUTRON-CAPTURE THERAPY OF CANCER [J].

HAWTHORNE, MF .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (07) :950-984