Chlorodinitrophenylhydrazine, a useful crystalline agent for absolute configuration determination of various chiral ketones

被引:6
作者
Kawai, Y [1 ]
Hayashi, M
Tokitoh, N
机构
[1] Nagahama Inst Biosci & Technol, Shiga 5260829, Japan
[2] Kyoto Univ, Chem Res Inst, Uji, Kyoto 6110011, Japan
关键词
phenylhydrazine chiral ketone; X-ray crystallography; absolute configuration;
D O I
10.1016/j.tet.2005.03.037
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
For the determination of absolute configuration of various chiral ketones, we examined some hydrazines having a heavy atom as crystalline auxiliaries, and found that 2-chloro-4,6-dinitrophenylhydrazine is a useful crystalline agent for carbonyl compounds. Chiral hydrazones prepared from the hydrazine and various chiral ketones gave suitable single crystals for X-ray crystallographic analysis. The absolute configurations of the hydrazones were determined by X-ray crystallographic analysis using anomalous dispersion effect of the chlorine atom. The hydrazine is a useful crystalline agent for absolute configuration determination of various chiral ketones. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5049 / 5055
页数:7
相关论文
共 44 条
[1]   SIR97:: a new tool for crystal structure determination and refinement [J].
Altomare, A ;
Burla, MC ;
Camalli, M ;
Cascarano, GL ;
Giacovazzo, C ;
Guagliardi, A ;
Moliterni, AGG ;
Polidori, G ;
Spagna, R .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1999, 32 :115-119
[2]  
BEURSKENS PT, DIRDIF 99 PROGRAM SY
[3]   On 2.4-dinitro-5-chlorine-phenylhydrazine and 2.4-dinitro-1.5-dihydrazino-benzene. [J].
Borsche, W .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1921, 54 :669-684
[4]  
EBATA T, 1987, AGR BIOL CHEM TOKYO, V51, P2925
[5]   ASYMMETRIC SYNTHESIS OF ALPHA-SUBSTITUTED KETONES BY METALATION AND ALKYLATION OF CHIRAL HYDRAZONES [J].
ENDERS, D ;
EICHENAUER, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1976, 15 (09) :549-551
[6]   ASYMMETRIC SYNTHESES VIA METALATED CHIRAL HYDRAZONES - OVERALL ENANTIOSELECTIVE ALPHA-ALKYLATION OF ACYCLIC KETONES [J].
ENDERS, D ;
EICHENAUER, H ;
BAUS, U ;
SCHUBERT, H ;
KREMER, KAM .
TETRAHEDRON, 1984, 40 (08) :1345-1359
[7]   ENANTIOSELECTIVE ALKYLATION OF CHIRAL ENOLATES [J].
EVANS, DA ;
TAKACS, JM .
TETRAHEDRON LETTERS, 1980, 21 (44) :4233-4236
[8]  
Fehr C., 1996, Angew. Chem., V35, P2566
[9]   ON ENANTIOMORPH-POLARITY ESTIMATION [J].
FLACK, HD .
ACTA CRYSTALLOGRAPHICA SECTION A, 1983, 39 (NOV) :876-881
[10]   ENANTIOFACIAL PROTONATION BY CATALYTIC ANTIBODIES [J].
FUJII, I ;
LERNER, RA ;
JANDA, KD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (22) :8528-8529