Novel chiral 1-(ferrocenylalkyl)-(S)-prolinols and their application in enantioselective synthesis

被引：16

作者：

Gotov, B

Toma, S ^{[1
]}

Solcániová, E

Cvengros, J

机构：

[1] Comenius Univ, Fac Nat Sci, Dept Organ Chem, Bratislava 84215, Slovakia

[2] Comenius Univ, Fac Nat Sci, Inst Chem, Bratislava 84215, Slovakia

来源：

TETRAHEDRON | 2000年 / 56卷 / 04期

关键词：

enantioselective synthesis; ferrocenylphosphine ligands; prolinol;

D O I：

10.1016/S0040-4020(99)01040-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diastereomeric ferrocenylphosphine ligands, (-)-(S,R,pS)-BPPF-Pro (3a) and (+)-(S,S,pR)-BPPF-Pro (3b), containing the (S)-prolinol moiety were prepared. A detailed structural elucidation of these ligands was carried out using NMR. The Pd-complexes of these ligands were used for enantioselective catalysis of allylic substitution reactions of rac-(E)-1,3-diphenyl-3-acetoxyprop-1-ene with C-nucleophiles generated from pentan-2,4-dione and dimethyl malonate. A series of chiral ferrocene aminoalcohols with (S)-prolinol moiety (4a-c) were also prepared. The role of the configuration of stereogenic centers for stereoselectivity in diethylzinc addition to benzaldehyde was studied. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：671 / 675

页数：5

共 16 条

[1] Planar-chiral ferrocenes in asymmetric catalysis:: The impact of stereochemically inhomogeneous ligands
Bolm, C
Muñiz, K
Hildebrand, JP
[J]. ORGANIC LETTERS, 1999, 1 (03) : 491 - 493
[2] On the role of planar chirality in asymmetric catalysis:: A study toward appropriate ferrocene ligands for diethylzinc additions
Bolm, C
Muñiz-Fernández, K
Seger, A
Raabe, G
Günther, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) : 7860 - 7867
[3] 1,8-NAPHTHALENEDIYLBIS(DIMETHYLPHOSPHANE) - STERIC INFLUENCE ON METHYLATION AND BORYLATION
COSTA, T
SCHMIDBAUR, H
[J]. CHEMISCHE BERICHTE-RECUEIL, 1982, 115 (04): : 1374 - 1378
[4] Enders D., 1993, ORG SYNTH, V8, P26
[5] A novel approach to ferrocenes with planar chirality
Ganter, C
Wagner, T
[J]. CHEMISCHE BERICHTE, 1995, 128 (12) : 1157 - 1161
[6] LANTHANOIDS IN ORGANIC-SYNTHESIS .6. THE REDUCTION OF ALPHA-ENONES BY SODIUM-BOROHYDRIDE IN THE PRESENCE OF LANTHANOID CHLORIDES - SYNTHETIC AND MECHANISTIC ASPECTS
GEMAL, AL
LUCHE, JL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (18) : 5454 - 5459
[7] MODIFICATION OF OPTICALLY-ACTIVE FERROCENYLPHOSPHINE LIGANDS FOR PALLADIUM-CATALYZED ASYMMETRIC ALLYLIC ALKYLATION
HAYASHI, T
YAMAMOTO, A
HAGIHARA, T
ITO, Y
[J]. TETRAHEDRON LETTERS, 1986, 27 (02) : 191 - 194
[8] ASYMMETRIC-SYNTHESIS CATALYZED BY CHIRAL FERROCENYLPHOSPHINE-TRANSITION-METAL COMPLEXES .5. PALLADIUM-CATALYZED ASYMMETRIC ALLYLATION OF ACTIVE METHINE COMPOUNDS
HAYASHI, T
KANEHIRA, K
HAGIHARA, T
KUMADA, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (01) : 113 - 120
[9] ASYMMETRIC-SYNTHESIS CATALYZED BY CHIRAL FERROCENYLPHOSPHINE-TRANSITION METAL-COMPLEXES .1. PREPARATION OF CHIRAL FERROCENYLPHOSPHINES
HAYASHI, T
MISE, T
FUKUSHIMA, M
KAGOTANI, M
NAGASHIMA, N
HAMADA, Y
MATSUMOTO, A
KAWAKAMI, S
KONISHI, M
YAMAMOTO, K
KUMADA, M
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1980, 53 (04) : 1138 - 1151
[10] KNOX GR, UNPUB

← 1 2 →