Practical asymmetric synthesis of β-trichloromethyl-β-hydroxy ketones by the reaction of chloral or chloral hydrate with chiral imines

被引:9
作者
Funabiki, K [1 ]
Honma, N [1 ]
Hashimoto, W [1 ]
Matsui, M [1 ]
机构
[1] Gifu Univ, Fac Engn, Dept Mat Sci & Technol, Gifu 5011193, Japan
关键词
D O I
10.1021/ol034461b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chloral or its hydrate undergoes the carbon-carbon bond-formation reaction with various optically active imines in the absence of any additive, followed by hydrolysis, to produce the corresponding beta-trichloromethyl-beta-hydroxy ketones in good yields with high enantioselectivities. In addition, the products with higher ee values were obtained by a simple recrystallization process.
引用
收藏
页码:2059 / 2061
页数:3
相关论文
共 15 条
[1]  
Arend M, 1995, ANGEW CHEM INT EDIT, V34, P2639
[2]  
BRANNOCK KC, 1967, J ORG CHEM, V29, P2579
[3]   A CATALYTIC ENANTIOSELECTIVE SYNTHESIS OF CHIRAL MONOSUBSTITUTED OXIRANES [J].
COREY, EJ ;
HELAL, CJ .
TETRAHEDRON LETTERS, 1993, 34 (33) :5227-5230
[4]   A GENERAL, CATALYTIC, AND ENANTIOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS [J].
COREY, EJ ;
LINK, JO .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) :1906-1908
[5]   A NEW PROCESS FOR THE ENANTIOSELECTIVE SYNTHESIS OF CHIRAL ALPHA-ARYLOXY AND ALPHA-HYDROXY ACIDS [J].
COREY, EJ ;
LINK, JO .
TETRAHEDRON LETTERS, 1992, 33 (24) :3431-3434
[6]   Regioselective ring cleavage of chiral β-trichloromethyl-β-propiolactone with organoaluminum compounds for the synthesis of optically active intermediates [J].
Fujisawa, T ;
Ito, T ;
Nishiura, S ;
Shimizu, M .
TETRAHEDRON LETTERS, 1998, 39 (52) :9735-9738
[7]   Facile synthesis of (S)-beta-hydroxy-beta-trichloromethylated aromatic ketones by the regioselective ring cleavage of chiral beta-trichloromethyl-beta-propiolactone under the Friedel-Crafts conditions [J].
Fujisawa, T ;
Ito, T ;
Fujimoto, K ;
Shimizu, M ;
Wynberg, H ;
Staring, EGJ .
TETRAHEDRON LETTERS, 1997, 38 (09) :1593-1596
[8]   Improved stereoselectivity in the heterogeneous catalytic synthesis of enalapril obtained through multidimensional screening [J].
Huffman, MA ;
Reider, PJ .
TETRAHEDRON LETTERS, 1999, 40 (05) :831-834
[9]   Practical asymmetric synthetic route to 4,4,4-trifluoro-3-hydroxybutyrate: Head-to-tail and head-to-head crystallizations through double and single hydrogen bonds of hetero- and homochiral 4,4,4-trifluoro-3-hydroxybutyrophenones [J].
Ishii, A ;
Kanai, M ;
Higashiyama, K ;
Mikami, K .
CHIRALITY, 2002, 14 (09) :709-712
[10]   Reaction of cyclohexanone benzylimines with ethylidenemalonate diesters.: Diphenyl 2-ethylidenemalonate:: A highly electrophilic synthetic equivalent of crotonic esters [J].
Jabin, I ;
Revial, G ;
Monnier-Benoit, N ;
Netchitaïlo, P .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (01) :256-261