Catalytic, asymmetric synthesis of cyanohydrin esters: The effect of anhydride structure on enantioselectivity

被引:24
作者
Belokon, YN
Carta, P
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
关键词
cyanohydrin; catalyst; asymmetric; ester; titanium; salen;
D O I
10.2174/1570178043488617
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A bimetallic titanium(salen) complex has been shown to catalyse the asymmetric addition of potassium cyanide to aldehydes in the presence of a range of anhydrides. leading to cyanohydrin esters. Linear aliphatic anhydrides (acetic and propionic) gave products with higher enantiomeric purity than those obtained using pivalic or benzoic anhydrides.
引用
收藏
页码:81 / 83
页数:3
相关论文
共 21 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]   COBALT(II) CATALYZED REACTION OF ALKENES WITH ALIPHATIC-ALDEHYDES AND MOLECULAR-OXYGEN - SCOPE AND MECHANISM [J].
BHATIA, S ;
PUNNIYAMURTHY, T ;
BHATIA, B ;
IQBAL, J .
TETRAHEDRON, 1993, 49 (27) :6101-6122
[5]  
CANTACUZENE J, 1966, TETRAHEDRON LETT, V7, P2237
[6]   THE BENZIL DICYANOHYDRIN REARRANGEMENT ANALOGY WITH THE BENZIL CYANIDE REACTION [J].
CLERICI, A ;
PORTA, O .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (06) :1591-1592
[7]   REDUCTIVE COUPLING OF BENZOYL CYANIDE AND CARBONYL-COMPOUNDS BY AQUEOUS TI(III) IONS - A NEW CONVENIENT AND SELECTIVE ACCESS TO THE LESS STABLE MIXED BENZOINS [J].
CLERICI, A ;
PORTA, O .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (10) :2889-2893
[8]   SYNTHESIS OF ALPHA-ALKOXYACRYLONITRILES USING SUBSTITUTED DIETHYL CYANOMETHYLPHOSPHONATES [J].
DINIZO, SE ;
FREERKSEN, RW ;
PABST, WE ;
WATT, DS .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (17) :2846-2849
[9]   ENZYMATIC RESOLUTION OF OPTICALLY-ACTIVE ALIPHATIC CYANOHYDRINS [J].
KANERVA, LT ;
KILJUNEN, E ;
HUUHTANEN, TT .
TETRAHEDRON-ASYMMETRY, 1993, 4 (11) :2355-2361
[10]   REACTIONS OF ALPHA-HYDROXY CARBONYL-COMPOUNDS WITH AZODICARBOXYLATES AND TRIPHENYLPHOSPHINE - SYNTHESIS OF ALPHA-N-HYDROXY AMINO-ACID DERIVATIVES [J].
KOLASA, T ;
MILLER, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (22) :4978-4984