P(i-PrNCH2CH2)3N as a Lewis Base Catalyst for the Synthesis of β-Hydroxynitriles Using TMSAN

被引:34
作者
Wadhwa, Kuldeep [1 ]
Verkade, John G. [1 ]
机构
[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA
基金
美国国家科学基金会;
关键词
CARBONYL-COMPOUNDS; EFFICIENT PROMOTER; HYDROXY NITRILES; COOPERATIVE CATALYSIS; COUPLING REACTIONS; ACETONITRILE; ALDEHYDES; ACTIVATION; TRIMETHYLSILYLACETONITRILE; PROAZAPHOSPHATRANES;
D O I
10.1021/jo900814t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Proazaphosphatrane 1a was found to be an efficient catalyst for synthesis of beta-hydroxynitriles via the reaction of trimethylsilylacetonitrile (TMSAN) with aldehydes under mild reaction conditions and typically low catalyst loading (ca. 2 mol%). A variety of functional groups were tolerated, and good to excellent product yields were obtained.
引用
收藏
页码:5683 / 5686
页数:4
相关论文
共 58 条
[21]   Lewis base-catalyzed cyanomethylation of carbonyl compounds with (trimethylsilyl)acetonitrile [J].
Kawano, Y ;
Kaneko, N ;
Mukaiyama, T .
CHEMISTRY LETTERS, 2005, 34 (11) :1508-1509
[22]  
KHAI BT, 1989, J ORG CHEM, V54, P949
[23]   P(RNCH2CH2)3N-catalyzed synthesis of β-hydroxy nitriles [J].
Kisanga, P ;
McLeod, D ;
D'Sa, B ;
Verkade, J .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09) :3090-3094
[24]   pKa measurements of P(RNCH2CH3)3N [J].
Kisanga, PB ;
Verkade, JG ;
Schwesinger, R .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (17) :5431-5432
[25]   A CONVENIENT METHOD FOR PREPARING ENANTIOMERICALLY PURE NORFLUOXETINE, FLUOXETINE AND TOMOXETINE [J].
KOENIG, TM ;
MITCHELL, D .
TETRAHEDRON LETTERS, 1994, 35 (09) :1339-1342
[26]   Highly (Z)-selective synthesis of β-monosubstituted α,β-unsaturated cyanides using the Peterson reaction [J].
Kojima, S ;
Fukuzaki, T ;
Yamakawa, A ;
Murai, Y .
ORGANIC LETTERS, 2004, 6 (22) :3917-3920
[27]   Cooperative catalysis of a cationic ruthenium complex, amine base, and Na salt: Catalytic activation of acetonitrile as a nucleophile [J].
Kumagai, N ;
Matsunaga, S ;
Shibasaki, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (42) :13632-13633
[28]   Catalytic nucleophilic activation of acetonitrile via a cooperative catalysis of cationic Ru complex, DBU, and NaPF6 [J].
Kumagai, Naoya ;
Matsunaga, Shigeki ;
Shibasaki, Masakatsu .
TETRAHEDRON, 2007, 63 (35) :8598-8608
[29]   ALKALI-METAL FLUORIDE MEDIATED SILYL-REFORMATSKY REACTION IN SOLID-LIQUID MEDIA - ACTIVATION BY MICROWAVES [J].
LATOUCHE, R ;
TEXIERBOULLET, F ;
HAMELIN, J .
TETRAHEDRON LETTERS, 1991, 32 (09) :1179-1182
[30]   PROTONATION OF ACYLLITHIUM REAGENTS BY ACETONITRILE - SYNTHESIS OF BETA-HYDROXY NITRILES [J].
LI, NS ;
YU, S ;
KABALKA, GW .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18) :5973-5974