Facile synthesis of chiral 2-formyl-1,1′-binaphthyl via lipase-catalyzed acylation and hydrolysis of 1,1′-binaphthyl oximes

被引:11
作者
Aoyagi, N [1 ]
Ohwada, T [1 ]
Izumi, T [1 ]
机构
[1] Yamagata Univ, Grad Sch Sci & Engn, Dept Chem & Chem Engn, Yamagata 9928510, Japan
关键词
binaphthyl; Suzuki cross-coupling; oxime; lipase; acylation; hydrolysis;
D O I
10.1016/j.tetlet.2003.09.061
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Lipase-catalyzed acylation of 2-hydroxyiminomethyl-1,1'-binaphthyl [(+/-)-1] and hydrolysis of 2-acetoxyiminomethyl-1,1'-bitiaphthyl [(+/-)-2] yielded optically active oximes 1 and 2 with high enantiomeric excess. Successful synthesis of the optically active aldehyde 4 from chiral O-acetyl oxime 2 occurred without a decrease of enantiomeric excess. (C) 2003 Elsevier Ltd. All riahts reserved.
引用
收藏
页码:8269 / 8272
页数:4
相关论文
共 33 条
[1]   Helical polyacetylene synthesized under chiral nematic liquid crystals [J].
Akagi, K ;
Piao, G ;
Kaneko, S ;
Higuchi, I ;
Shirakawa, H ;
Kyotani, M .
SYNTHETIC METALS, 1999, 102 (1-3) :1406-1409
[2]   Effect of the alkyl chain length of 1,1′-binaphthyl esters in lipase-catalyzed amidation [J].
Aoyagi, N ;
Kawauchi, S ;
Izumi, T .
TETRAHEDRON LETTERS, 2003, 44 (30) :5609-5612
[3]   Kinetic resolution of 1,1′-binaphthylamines via lipase-catalyzed amidation [J].
Aoyagi, N ;
Izumi, T .
TETRAHEDRON LETTERS, 2002, 43 (32) :5529-5531
[4]   STUDIES ON THE ENZYMATIC RESOLUTION OF CHIRAL TRICARBONYL(BENZALDEHYDE OXIME)CHROMIUM COMPLEXES [J].
BALDOLI, C ;
MAIORANA, S ;
CARREA, G ;
RIVA, S .
TETRAHEDRON-ASYMMETRY, 1993, 4 (05) :767-772
[5]   Novel concepts in directed biaryl synthesis, part 78. The lactone concept: An efficient pathway to axially chiral natural products and useful reagents [J].
Bringmann, G ;
Breuning, M ;
Tasler, S .
SYNTHESIS-STUTTGART, 1999, (04) :525-558
[6]  
Carrea G, 2000, ANGEW CHEM INT EDIT, V39, P2226
[7]   QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS [J].
CHEN, CS ;
FUJIMOTO, Y ;
GIRDAUKAS, G ;
SIH, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) :7294-7299
[8]   Anti-AIDS agents .26. Structure-activity correlations of gomisin-G-related anti-HIV lignans from Kadsura interior and of related synthetic analogues [J].
Chen, DF ;
Zhang, SX ;
Xie, L ;
Xie, JX ;
Chen, K ;
Kashiwada, Y ;
Zhou, BN ;
Wang, P ;
Cosentino, LM ;
Lee, KH .
BIOORGANIC & MEDICINAL CHEMISTRY, 1997, 5 (08) :1715-1723
[9]  
FABER K, 1992, SYNTHESIS-STUTTGART, P895
[10]  
FEITZON M, 1986, ORGANIC SYNTHESES OX, P503