Reactions on a solid surface.: A simple, economical, and efficient acylation of alcohols and Amines over Al2O3

被引：51

作者：

Yadav, VK ^{[1
]}

Babu, KG ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 02期

关键词：

D O I：

10.1021/jo035412f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Al2O3 brings about a rapid acylation of a range of alcohols and amines with acid chlorides and acid anhydrides, respectively. Amines are easily Boc- and Cbz-protected on reaction with Boc-anhydride and Cbz-Cl, respectively. The acylation of phenols is slow enough to allow chemoselective acylation of alcohols and amines in the presence of phenols.

引用

页码：577 / 580

页数：4

共 14 条

[1] Lipase-catalysed chemoselective monoacetylation of hydroxyalkylphenols and chemoselective removal of a single acetyl group from their diacetates [J].

Allevi, P ;

Ciuffreda, P ;

Longo, A ;

Anastasia, M .

TETRAHEDRON-ASYMMETRY, 1998, 9 (16) :2915-2924

[2] Indium(III) chloride as a new, highly efficient, and versatile catalyst for acylation of phenols, thiols, alcohols, and amines [J].

Chakraborti, AK ;

Gulhane, R .

TETRAHEDRON LETTERS, 2003, 44 (35) :6749-6753

[3] Fluoroboric acid adsorbed on silica gel as a new and efficient catalyst for acylation of phenols, thiols, alcohols, and amines [J].

Chakraborti, AK ;

Gulhane, R .

TETRAHEDRON LETTERS, 2003, 44 (17) :3521-3525

[4] Electrostatic catalysis by ionic aggregates:: scope and limitations of Mg(ClO4)2 as acylation catalyst [J].

Chakraborti, AK ;

Sharma, L ;

Gulhane, R ;

Shivani .

TETRAHEDRON, 2003, 59 (39) :7661-7668

[5] Perchloric acid adsorbed on silica gel as a new, highly efficient, and versatile catalyst for acetylation of phenols, thiols, alcohols, and amines [J].

Chakraborti, AK ;

Gulhane, R .

CHEMICAL COMMUNICATIONS, 2003, (15) :1896-1897

[6]

Greene T. W., 1999, PROTECTIVE GROUPS OR

[7] Efficient synthesis of (6R)-6-amino-1-methyl-4-(3-methylbenzyl)-hexahydro-1H-1,4-diazepine from methyl (2R)- and (2S)-1-benzyloxycarbonylaziridine-2-carboxylates [J].

Kato, S ;

Harada, H ;

Morie, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (21) :3219-3225

[8] Distannoxane-catalyzed highly selective acylation of alcohols [J].

Orita, A ;

Mitsutome, A ;

Otera, J .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) :2420-2421

[9] Ac2O-Py/basic alumina as a versatile reagent for acetylations in solvent-free conditions under microwave irradiation [J].

Paul, S ;

Nanda, P ;

Gupta, R ;

Loupy, A .

TETRAHEDRON LETTERS, 2002, 43 (23) :4261-4265

[10]

POSNER GH, 1981, SYNTHESIS-STUTTGART, P789

← 1 2 →