Synthesis of chiral plane-extended pyridyl alcohols for the enantioselective addition of diethylzinc to aldehydes

被引:28
作者
Kang, JY [1 ]
Kim, HY
Kim, JH
机构
[1] Sogang Univ, Dept Chem, Seoul 121742, South Korea
[2] Korea Inst Sci & Technol, Biochem Res Ctr, Seoul 130650, South Korea
关键词
D O I
10.1016/S0957-4166(99)00247-5
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Enantiomerically pure pyridyl alcohols, 1 and 2, were prepared from readily available racemic pyridyl alcohol 3 and applied to the enantioselective addition of diethylzinc to aldehydes resulting in moderately high enantiomeric excess (90%) in the case of benzaldehyde. In this study the first example of an alteration in the configuration of the product upon change of a non-chiral and non-coordinating part of the catalyst was observed. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2523 / 2533
页数:11
相关论文
共 34 条
[1]   ASYMMETRIC ADDITION OF DIETHYLZINC TO AROMATIC-ALDEHYDES USING ENANTIOMERICALLY PURE HYDROXYMETHYL OXAZOLINE LIGANDS [J].
ALLEN, JV ;
FROST, CG ;
WILLIAMS, JMJ .
TETRAHEDRON-ASYMMETRY, 1993, 4 (04) :649-650
[2]   REARRANGEMENTS OF N-OXIDES - A NOVEL SYNTHESIS OF PYRIDYL CARBINOLS AND ALDEHYDES [J].
BOEKELHEIDE, V ;
LINN, WJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (05) :1286-1291
[3]   CATALYZED ENANTIOSELECTIVE ALKYLATION OF ALDEHYDES [J].
BOLM, C ;
SCHLINGLOFF, G ;
HARMS, K .
CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (05) :1191-1203
[4]   ELECTRONIC EFFECTS IN STEREOCHEMISTRY .3. ASYMMETRIC REDUCTION OF PHENYLALKYLKETONES DIVERSELY SUBSTITUTED BY CHIRAL AROMATIC ORGANOMAGNESIUM COMPOUNDS [J].
CAPILLON, J ;
GUETTE, JP .
TETRAHEDRON, 1979, 35 (15) :1817-1820
[5]   DIASTEREOISOMERIC PURE 2-(1-HYDROXYALKYL)PYRIDINES AS CATALYSTS IN THE ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES [J].
CHELUCCI, G ;
SOCCOLINI, F .
TETRAHEDRON-ASYMMETRY, 1992, 3 (10) :1235-1238
[6]   BETA-ACYLETHYLATION WITH KETONIC MANNICH BASES - THE SYNTHESIS OF SOME DIKETONES, KETONIC SULFIDES, NITROKETONES AND PYRIDINES [J].
GILL, NS ;
JAMES, KB ;
LIONS, F ;
POTTS, KT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (19) :4923-4928
[7]  
Hahn W. E., 1963, ROCZNIKI CHEM, V37, P403
[8]   ASYMMETRIC EPOXIDATION MODELS - AN ALKYL HYDROPEROXIDE DEPENDENT CHANGE IN MECHANISM [J].
HAWKINS, JM ;
SHARPLESS, KB .
TETRAHEDRON LETTERS, 1987, 28 (25) :2825-2828
[9]  
HONES GB, 1993, TETRAHEDRON-ASYMMETR, V4, P261
[10]   CATALYZED ASYMMETRIC REACTION OF ALDEHYDES WITH DIALKYLZINC IN THE PRESENCE OF CHIRAL PYRIDYL ALCOHOLS AS LIGANDS [J].
ISHIZAKI, M ;
FUJITA, K ;
SHIMAMOTO, M ;
HOSHINO, O .
TETRAHEDRON-ASYMMETRY, 1994, 5 (03) :411-424