Catalytic, asymmetric synthesis of cyanohydrin ethyl carbonates

被引:105
作者
Belokon, YN
Blacker, AJ
Clutterbuck, LA
North, M [1 ]
机构
[1] Kings Coll London, Dept Chem, London WC2R 2LS, England
[2] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, Russia
[3] Avecia Ltd, Huddersfield HD2 1GA, W Yorkshire, England
关键词
D O I
10.1021/ol035828f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The bimetallic titanium complex [(salen)TiO](2), where salen is the ligand derived from (R,R)-cyclohexanediamine and 3,5-di-tert-butyl-salicylaldehyde, has been shown to catalyze the asymmetric addition of ethyl cyanoformate to aldehydes leading to cyanohydrin carbonates with high enantiomeric excesses.
引用
收藏
页码:4505 / 4507
页数:3
相关论文
共 16 条
[1]  
Belokon YN, 2002, HELV CHIM ACTA, V85, P3301, DOI 10.1002/1522-2675(200210)85:10<3301::AID-HLCA3301>3.0.CO
[2]  
2-2
[3]   Catalytic asymmetric synthesis of O-acetyl cyanohydrins from KCN, Ac2O and aldehydes [J].
Belokon, YN ;
Gutnov, AV ;
Moskalenko, MA ;
Yashkina, LV ;
Lesovoy, DE ;
Ikonnikov, NS ;
Larichev, VS ;
North, M .
CHEMICAL COMMUNICATIONS, 2002, (03) :244-245
[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]   O-Methoxycarbonyl cyanohydrin as a new protective group for carbonyls [J].
Berthiaume, D ;
Poirier, D .
TETRAHEDRON, 2000, 56 (33) :5995-6003
[9]   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
[10]   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