Proline-catalyzed direct asymmetric aldol reaction of trifluoroacetaldehyde ethyl hemiacetal with ketones

被引:31
作者
Funabiki, Kazumasa [1 ]
Yamamoto, Hitoshi [1 ]
Nagaya, Hideyuki [1 ]
Matsui, Masaki [1 ]
机构
[1] Gifu Univ, Fac Engn, Dept Mat Sci & Technol, Gifu 5011193, Japan
关键词
fluorine and compounds; aldol reactions; amino acids and derivatives; asymmetric reactions;
D O I
10.1016/j.tetlet.2006.05.165
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
L-Proline-catalyzed direct asymmetric aldol reaction of trifluoroacetaldehyde ethyl hemiacetal with unmodified ketones smoothly occurred at ambient temperature to produce beta-hydroxy-beta-trifluoromethylated ketones with good to excellent diastereo (up to 96% de) and enantioselectivities (up to 91% ee). (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5507 / 5510
页数:4
相关论文
共 27 条
[11]   Enamine-assisted facile generation of trifluoroacetaldehyde from trifluoroacetaldehyde ethyl hemiacetal and its carbon-carbon bond forming reaction leading to β-hydroxy-β-trifluoromethyl ketones [J].
Funabiki, K ;
Nojiri, M ;
Matsui, M ;
Shibata, K .
CHEMICAL COMMUNICATIONS, 1998, (18) :2051-2052
[12]  
FUNABIKI K, 2005, ACS SYM SER, V911, P342
[13]   Asymmetric synthesis of β-hydroxy-β-trifluoromethylated ketones via in situ generation of trifluoroacetaldehyde and its asymmetric carbon-carbon bond formation reaction with chiral imines in aqueous media [J].
Funabiki, Kazumasa ;
Hasegawa, Kazutoshi ;
Murase, Yoshihiro ;
Nagaya, Hideyuki ;
Matsui, Masaki .
JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (4-5) :545-547
[14]   Direct aldol reaction of trifluoroacetaldehyde ethyl hemiacetal with ketones by use of the combination of amines and acids [J].
Funabiki, Kazumasa ;
Nagaya, Hideyuki ;
Ishihara, Mika ;
Matsui, Masaki .
TETRAHEDRON, 2006, 62 (21) :5049-5053
[15]   Highly enantioselective synthesis of fluorinated γ-amino alcohols through proline-catalyzed cross-Mannich reaction [J].
Fustero, S ;
Jiménez, D ;
Sanz-Cervera, JF ;
Sánchez-Roselló, M ;
Esteban, E ;
Simón-Fuentes, A .
ORGANIC LETTERS, 2005, 7 (16) :3433-3436
[16]   THE PREPARATION OF TRIFLUORINATED ALDEHYDES [J].
HENNE, AL ;
PELLEY, RL ;
ALM, RM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (08) :3370-3371
[17]   Catalytic asymmetric synthesis of chiral fluoroorganic compounds [J].
Iseki, K .
TETRAHEDRON, 1998, 54 (46) :13887-13914
[18]   Trifluoroacetaldehyde [J].
Ishii, A ;
Takeda, Y .
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1999, 57 (10) :898-900
[19]   NUCLEAR MAGNETIC-RESONANCE STUDY OF HYDROGEN-BONDING IN 1,1,1-TRIFLUORO-2-HYDROXY-4-ALKANONES [J].
KIEHLMANN, E ;
MENON, BC ;
MCGILLIV.N .
CANADIAN JOURNAL OF CHEMISTRY, 1973, 51 (19) :3177-3181
[20]   FACILE SYNTHESIS OF ALPHA-TRIFLUOROMETHYLATED ALCOHOLS FROM TRIFLUOROACETALDEHYDE ETHYL HEMIACETAL [J].
KUBOTA, T ;
IIJIMA, M ;
TANAKA, T .
TETRAHEDRON LETTERS, 1992, 33 (10) :1351-1354