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
[31]   Michellamine alkaloids inhibit protein kinase C [J].
White, EL ;
Chao, WR ;
Ross, LJ ;
Borhani, DW ;
Hobbs, PD ;
Upender, V ;
Dawson, MI .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1999, 365 (01) :25-30
[32]   Methylenedioxy group and cyclooctadiene ring as structural determinants of schisandrin in protecting against myocardial ischemia-reperfusion injury in rats [J].
Yim, TK ;
Ko, KM .
BIOCHEMICAL PHARMACOLOGY, 1999, 57 (01) :77-81
[33]  
ZHIYI LK, 1996, CANC LETT, V108, P67