Importance of chiral phase-transfer catalysts with dual functions in obtaining high enantioselectivity in the Michael reaction of malonates and chalcone derivatives

被引:114
作者
Ooi, T [1 ]
Ohara, D [1 ]
Fukumoto, K [1 ]
Maruoka, K [1 ]
机构
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan
关键词
D O I
10.1021/ol050902a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Highly enantioselective Michael addition of diethyl malonate to chalcone derivatives has been achieved under mild phase-transfer conditions by the successful utilization of N-spiro C-2-symmetric chiral quaternary ammonium bromide 1 as a catalyst, which possesses diarylhydroxymethyl functionalities as a recognition site for the prochiral electrophile. This simple asymmetric Michael addition process was found to be quite effective for various chalcone derivatives, including those with heteroaromatic substituents.
引用
收藏
页码:3195 / 3197
页数:3
相关论文
共 33 条
[1]   Asymmetric Weitz-Scheffer epoxidation of isoflavones with hydroperoxides mediated by optically active phase-transfer catalysts [J].
Adam, W ;
Rao, PB ;
Degen, HG ;
Levai, A ;
Patonay, T ;
Saha-Möller, CR .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (01) :259-264
[2]   Synthesis and applications of C2-symmetric guanidine bases [J].
Allingham, MT ;
Howard-Jones, A ;
Murphy, PJ ;
Thomas, DA ;
Caulkett, PWR .
TETRAHEDRON LETTERS, 2003, 44 (48) :8677-8680
[3]   One-pot synthesis of α-diazo-β-hydroxyesters under phase-transfer catalysis and application to the catalytic asymmetric aldol reaction [J].
Arai, S ;
Hasegawa, K ;
Nishida, A .
TETRAHEDRON LETTERS, 2004, 45 (05) :1023-1026
[4]   Catalytic asymmetric epoxidation of enones under phase-transfer catalyzed conditions [J].
Arai, S ;
Tsuge, H ;
Oku, M ;
Miura, M ;
Shioiri, T .
TETRAHEDRON, 2002, 58 (08) :1623-1630
[5]   Asymmetric cyclopropanation reaction under phase-transfer catalyzed conditions [J].
Arai, S ;
Nakayama, K ;
Ishida, T ;
Shioiri, T .
TETRAHEDRON LETTERS, 1999, 40 (22) :4215-4218
[6]   Asymmetric C-C bond forming reactions with chiral crown catalysts derived from D-glucose and D-galactose [J].
Bakó, P ;
Czinege, E ;
Bakó, T ;
Czugler, M ;
Toke, L .
TETRAHEDRON-ASYMMETRY, 1999, 10 (23) :4539-4551
[7]   Phase-transfer catalyzed asymmetric epoxidation of chalcones using chiral crown ethers derived from D-glucose, D-galactose, and D-mannitol [J].
Bakó, T ;
Bakó, P ;
Keglevich, G ;
Bombicz, P ;
Kubinyi, M ;
Pál, K ;
Bodor, S ;
Makó, A ;
Töke, L .
TETRAHEDRON-ASYMMETRY, 2004, 15 (10) :1589-1595
[8]  
Bhunnoo RA, 2002, ANGEW CHEM INT EDIT, V41, P3479, DOI 10.1002/1521-3773(20020916)41:18<3479::AID-ANIE3479>3.0.CO
[9]  
2-O
[10]  
Brown RCD, 2001, ANGEW CHEM INT EDIT, V40, P4496, DOI 10.1002/1521-3773(20011203)40:23<4496::AID-ANIE4496>3.0.CO