Chemoselective activation of aldimine in preference to aldehyde by the combination of BF3•OEt2 and water:: Novel catalyst for the Mannich-type reaction

被引:28
作者
Akiyama, T [1 ]
Takaya, J [1 ]
Kagoshima, H [1 ]
机构
[1] Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan
关键词
D O I
10.1246/cl.1999.947
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Reported herein are that catalytic amount of conventional Lewis acids activated aldimines in preference to aldehydes, and addition of water to BF3. OEt2 accelerated the Mannich-type reaction significantly to afford p-amino carbonyl compounds in high yields.
引用
收藏
页码:947 / 948
页数:2
相关论文
共 27 条
[1]  
Akiyama T, 1998, SYNLETT, P273
[2]   HBF4 catalyzed Mannich-type reaction in aqueous media [J].
Akiyama, T ;
Takaya, J ;
Kagoshima, H .
SYNLETT, 1999, (07) :1045-1048
[3]  
ARENDT FM, 1998, ANGEW CHEM INT EDIT, V37, P1044
[4]   Ytterbium triflate catalysed allylation of aldehydes: An unusual benzoic acid induced acceleration [J].
Aspinall, HC ;
Greeves, N ;
McIver, EG .
TETRAHEDRON LETTERS, 1998, 39 (50) :9283-9286
[5]   Additions of organometallic reagents to C=N bonds: Reactivity and selectivity [J].
Bloch, R .
CHEMICAL REVIEWS, 1998, 98 (04) :1407-1438
[6]  
COTTON FA, 1986, ADV INORG CHEM, P174
[7]   Catalytic, enantioselective alkylation of α-imino esters using late transition metal phosphine complexes as catalysts [J].
Ferraris, D ;
Young, B ;
Dudding, T ;
Lectka, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (18) :4548-4549
[8]   Mechanism of palladium complex-catalyzed enantioselective Mannich-type reaction: Characterization of a novel binuclear palladium enolate complex [J].
Fujii, A ;
Hagiwara, E ;
Sodeoka, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (23) :5450-5458
[9]  
ISHIHARA K, 1994, SYNLETT, P963
[10]   A NEW CHIRAL BLA PROMOTER FOR ASYMMETRIC AZA-DIELS-ALDER AND ALDOL-TYPE REACTIONS OF IMINES [J].
ISHIHARA, K ;
MIYATA, M ;
HATTORI, K ;
TADA, T ;
YAMAMOTO, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (23) :10520-10524