Enantioselective addition of organometallics to aldehydes using camphor derived chiral 1,4-aminoalcohols as ligands

被引:47
作者
Knollmüller, M [1 ]
Ferencic, M [1 ]
Gärtner, P [1 ]
机构
[1] Vienna Univ Technol, Inst Organ Chem, A-1060 Vienna, Austria
关键词
D O I
10.1016/S0957-4166(99)00413-9
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
(+)-Camphor derived enantiomerically pure 1,4-aminoalcohols have been used as ligands in the addition reactions of n-BuLi and n-BuMgBr to benzaldehyde and in the reaction of diethylzinc with benzaldehyde and hexanal. All chiral secondary alcohols were obtained in good chemical yields and enantioselectivities were up to 87% ee in the addition of diethylzinc. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3969 / 3975
页数:7
相关论文
共 37 条
[1]   1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].
Ager, DJ ;
Prakash, I ;
Schaad, DR .
CHEMICAL REVIEWS, 1996, 96 (02) :835-875
[2]   Control of the enantiochemistry of electrophilic substitutions of N-pivaloyl-alpha-lithio-o-ethylaniline: Stereoinformation transfer based on the method of organolithium formation [J].
Basu, A ;
Beak, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (06) :1575-1576
[3]   THE CHIRAL POOL AS A SOURCE OF ENANTIOSELECTIVE CATALYSTS AND AUXILIARIES [J].
BLASER, HU .
CHEMICAL REVIEWS, 1992, 92 (05) :935-952
[4]  
CHO BT, 1994, TETRAHEDRON LETT, V35, P4115
[5]   Catalytic enantioselective reactions .9. 1,2-O-isopropylidene-5-deoxy-5-N,N-dialkyl (or -N-monoalkyl)amino-alpha-D-xylofuranose derivatives as highly-effective chiral catalysts for enantioselective addition of diethylzinc to aliphatic and aromatic aldehydes [J].
Cho, BT ;
Kim, N .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (24) :2901-2907
[6]   Enantioselective addition of diethylzinc to aldehydes catalyzed by a new chiral β-amino alcohol derived from D-mannitol [J].
Cho, BT ;
Chun, YS .
TETRAHEDRON-ASYMMETRY, 1998, 9 (09) :1489-1492
[7]   Synthesis of new enantiopure gamma-aminoalcohols: Their use as catalysts in the alkylation of benzaldehyde by diethylzinc [J].
Cicchi, S ;
Crea, S ;
Goti, A ;
Brandi, A .
TETRAHEDRON-ASYMMETRY, 1997, 8 (02) :293-301
[8]   Structure-selectivity relationship in alkyllithium-aldehyde condensations using 3-aminopyrrolidine lithium amides as chiral auxiliaries [J].
Corruble, A ;
Valnot, JY ;
Maddaluno, J ;
Duhamel, P .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) :8266-8275
[9]   ENANTIOSELECTIVE ADDITION OF N-BUTYLLITHIUM TO BENZALDEHYDE IN THE PRESENCE OF CHIRAL LITHIUM AMIDES [J].
ELEVELD, MB ;
HOGEVEEN, H .
TETRAHEDRON LETTERS, 1984, 25 (45) :5187-5190
[10]   STEREOSELECTIVE ORGANIC-REACTIONS - CATALYSTS FOR CARBONYL ADDITION PROCESSES [J].
EVANS, DA .
SCIENCE, 1988, 240 (4851) :420-426