Catalyst-free DMSO-promoted synthesis of cyanohydrin carbonates from aldehydes

被引:46
作者
Iwanami, K [1 ]
Hinakubo, Y [1 ]
Oriyama, T [1 ]
机构
[1] Ibaraki Univ, Fac Sci, Mito, Ibaraki 3108512, Japan
关键词
cyanation; cyanohydrin carbonate; cyanoformate; aldehyde; DMSO;
D O I
10.1016/j.tetlet.2005.06.128
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A variety of cyanohydrin carbonates were readily prepared from aldehydes with cyanoformate in DMSO using no catalyst in a convenient one-pot procedure. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5881 / 5883
页数:3
相关论文
共 29 条
[1]   Trimethylsilyl cyanide addition to carbonyl compounds under neutral condition catalyzed by iodine [J].
Azizi, N ;
Saidi, MR .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2003, 178 (10) :2111-2115
[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]   Chemically catalyzed asymmetric cyanohydrin syntheses [J].
Brunel, JM ;
Holmes, IP .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (21) :2752-2778
[4]   Enantioselective cyanoformylation of aldehydes mediated by BINOLAM-AlCl as a monometallic bifunctional catalyst [J].
Casas, J ;
Baeza, A ;
Sansano, JM ;
Nájera, C ;
Saá, JM .
TETRAHEDRON-ASYMMETRY, 2003, 14 (02) :197-200
[5]   Synthesis of racemic tertiary cyanohydrins [J].
Chen, FX ;
Feng, XM .
SYNLETT, 2005, (06) :892-899
[6]   PREPARATION OF CYANOFORMATES - CROWN ETHER PHASE TRANSFER CATALYSIS [J].
CHILDS, ME ;
WEBER, WP .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (21) :3486-3487
[7]   A two-step procedure for the conversion of α,β-unsaturated aldehydes into γ-azido-α,β-unsaturated nitriles [J].
Deardorff, DR ;
Taniguchi, CM ;
Tafti, SA ;
Kim, HY ;
Choi, SY ;
Downey, KJ ;
Nguyen, TV .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (21) :7191-7194
[8]   CYANOSILYLATION OF ALDEHYDES AND KETONES - CONVENIENT ROUTE TO CYANOHYDRIN DERIVATIVES [J].
EVANS, DA ;
TRUESDALE, LK ;
CARROLL, GL .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (02) :55-56
[9]  
EVANS DA, 1973, TETRAHEDRON LETT, V49, P4929
[10]   ADDITION OF TERT-BUTYLDIMETHYLSILYL OR TERT-BUTYLDIPHENYLSILYL CYANIDE TO HINDERED KETONES [J].
GOLINSKI, M ;
BROCK, CP ;
WATT, DS .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (01) :159-164