Highly efficient double-activation catalysts for the synthesis of ketone cyanohydrins

被引：19

作者：

Chen, FX

Liu, XH

Qin, B

Zhou, H

Feng, XM ^{[1
]}

Zhang, GL

机构：

[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China

[2] Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2004年 / 14期

关键词：

addition reactions; aluminum; ketones; Schiff bases; nitriles;

D O I：

10.1055/s-2004-831167

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tertiary cyanohydrin trimethylsilyl ethers were synthesized in excellent chemical yields by using salen-Al complex (0.25 mol%) and N-oxide (0.5 mol%) without solvent at ambient temperature. The relationship between the ligand structure and catalyst efficiency is discussed. Preliminary mechanistic studies were carried out, and transition states were proposed accounting for the action of the double-activation catalysts.

引用

收藏

页码：2266 / 2272

页数：7

相关论文

共 59 条

[1] Group 13 compounds incorporating salen ligands [J].

Atwood, DA ;

Harvey, MJ .

CHEMICAL REVIEWS, 2001, 101 (01) :37-52

[2] Indium tribromide:: a highly effective catalyst for the addition of trimethylsilyl cyanide to α-hetero-substituted ketones [J].

Bandini, M ;

Cozzi, PG ;

Melchiorre, P ;

Umani-Ronchi, A .

TETRAHEDRON LETTERS, 2001, 42 (16) :3041-3043

[3]

Bandini M, 2002, EUR J ORG CHEM, V2002, P3243

[4] The asymmetric addition of trimethylsilyl cyanide to aldehydes catalyzed by chiral (salen)titanium complexes [J].

Belokon, YN ;

Caveda-Cepas, S ;

Green, B ;

Ikonnikov, NS ;

Krustalev, VN ;

Larichev, VS ;

Moscalenko, MA ;

North, M ;

Orizu, C ;

Tararov, VI ;

Tasinazzo, M ;

Timofeeva, GI ;

Yashkina, LV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (16) :3968-3973

[5] The asymmetric addition of trimethylsilyl cyanide to ketones catalysed by a bimetallic, chiral (salen)titanium complex [J].

Belokon, YN ;

Green, B ;

Ikonnikov, NS ;

North, M ;

Tararov, VI .

TETRAHEDRON LETTERS, 1999, 40 (46) :8147-8150

[6] Optimized catalysts for the asymmetric addition of trimethylsilyl cyanide to aldehydes and ketones [J].

Belokon, YN ;

Green, B ;

Ikonnikov, NS ;

North, M ;

Parsons, T ;

Tararov, VI .

TETRAHEDRON, 2001, 57 (04) :771-779

[7]

Belokon' YN, 2000, EUR J ORG CHEM, V2000, P2655

[8] Synthesis of cyanohydrin trimethylsilyl ethers of acylferrocenes [J].

Bian, ZX ;

Zhao, HY ;

Li, BG .

POLYHEDRON, 2003, 22 (12) :1523-1528

[9] Double activation of constrained geometry and ansa-metallocene group 4 metal Dialkyls:: Synthesis, structure, and olefin polymerization study of mono-and dicationic aluminate complexes [J].

Chen, EYX ;

Kruper, WJ ;

Roof, G ;

Wilson, DR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (04) :745-746

[10] Enantioselective cyanosilylation of ketones by a catalytic double-activation method employing chiral Lewis acid and achiral N-oxide catalysts [J].

Chen, FX ;

Feng, XM ;

Qin, B ;

Zhang, GL ;

Jiang, YZ .

ORGANIC LETTERS, 2003, 5 (06) :949-952

← 1 2 3 4 5 6 →