First catalytic, enantioselective aldol-Tishchenko reactions with ketone aldols as enol equivalents

被引:36
作者
Schneider, C [1 ]
Hansch, M [1 ]
机构
[1] Univ Gottingen, Inst Organ Chem, D-37077 Gottingen, Germany
关键词
aldol reaction; asymmetric catalysis; ketone aldols; Tishchenko reduction; zirconium;
D O I
10.1055/s-2003-38741
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chiral zirconiumTADDOLates were found to catalyze the aldol-Tishchenko reaction of diacetone alcohol (1a) and two other ketone aldol adducts 1b and 1c with a range of aldehydes giving rise to differentiated 1,3-anti-diol monoesters in good yields, complete diastereocontrol and moderate enantioselectivities.
引用
收藏
页码:837 / 840
页数:4
相关论文
共 42 条
[21]   Catalytic asymmetric acyl halide-aldehyde cyclocondensations. A strategy for enantioselective catalyzed cross aldol reactions [J].
Nelson, SG ;
Peelen, TJ ;
Wan, ZH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (41) :9742-9743
[22]   Catalyzed enantioselective aldol additions of latent enolate equivalents [J].
Nelson, SG .
TETRAHEDRON-ASYMMETRY, 1998, 9 (03) :357-389
[23]  
NOTHRUP AB, 2002, J AM CHEM SOC, V124, P6798
[24]  
Palomo C, 2002, CHEM-EUR J, V8, P37, DOI 10.1002/1521-3765(20020104)8:1<36::AID-CHEM36>3.0.CO
[25]  
2-L
[26]   Contrasting steric effects of the ketones and aldehydes in the reactions of the diisopinocampheyl enolborinates of methyl ketones with aldehydes [J].
Ramachandran, PV ;
Xu, WC ;
Brown, HC .
TETRAHEDRON LETTERS, 1996, 37 (28) :4911-4914
[27]   Zr(OtBu)4-catalysed synthesis of acetone aldol adducts and domino aldol-Tishchenko reactions with diacetone alcohol as enol equivalent [J].
Schneider, C ;
Hansch, M .
CHEMICAL COMMUNICATIONS, 2001, (13) :1218-1219
[28]  
Seebach D, 2001, ANGEW CHEM INT EDIT, V40, P92, DOI 10.1002/1521-3773(20010105)40:1<92::AID-ANIE92>3.3.CO
[29]  
2-B
[30]  
SEEBACH D, 2001, ANGEW CHEM, V113, P97