C-2-SYMMETRICAL BICYCLIC DIOLS AS CHIRAL LIGANDS IN THE TITANATE-CATALYZED ENANTIOSELECTIVE ADDITION OF ALKYLZINC REAGENTS TO ALDEHYDES

被引：42

作者：

WALDMANN, H ^{[1
]}

WEIGERDING, M ^{[1
]}

DREISBACH, C ^{[1
]}

WANDREY, C ^{[1
]}

机构：

[1] FORSCHUNGSZENTRUM JULICH, FORSCHUNGSZENTRUM, INST BIOTECHNOL, D-52425 JULICH, GERMANY

来源：

HELVETICA CHIMICA ACTA | 1994年 / 77卷 / 08期

关键词：

D O I：

10.1002/hlca.19940770803

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantiomerically pure C-2-symmetric 1,4-diols embodying bicyclic C-frameworks were synthesized by means of asymmetric carbo-Diels-Alder reactions as key steps (Scheme 1). They were investigated as chiral ligands in the enantioselective addition of ZnEt(2) to aromatic aldehydes. In the presence of 20-40 mol-% of the titanates formed from these diols and [Ti(i-PrO)(4)] at -78 degrees, the respective 1-arylpropanols were obtained with enantiomer ratios up to 93:7(Scheme 2, Table).

引用

页码：2111 / 2116

页数：6

共 50 条

[31] Enantioselective addition of diethylzinc to aldehydes with novel chiral C2-symmetric dimeric ligands
Okaniwa, M
Yanada, R
Ibuka, T
TETRAHEDRON LETTERS, 2000, 41 (07) : 1047 - 1050
[32] Solid-phase synthesis of chiral N-acylethylenediamines and their use as ligands for the asymmetric addition of alkylzinc and alkenylzinc reagents to aldehydes
Sprout, CM
Richmond, ML
Seto, CT
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (20): : 6666 - 6673
[33] Synthesis of new C2-symmetrical bissulfonamide ligands and application in the enantioselective addition of alkynylzinc to aldehydes and ketones
Ni, M
Wang, R
Han, ZJ
Mao, B
Da, CS
Liu, L
Chen, C
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) : 1659 - 1665
[34] Enantioselective rhodium-catalyzed addition of arylboronic acids to aldehydes using chiral spiro monophosphite ligands
Duan, HF
Xie, JH
Shi, WJ
Zhang, Q
Zhou, QL
ORGANIC LETTERS, 2006, 8 (07) : 1479 - 1481
[35] Enantioselective Addition of Diethylzinc to Aromatic Aldehydes Catalyzed by Modular Amino Acids and Phenylethanamine Based Chiral Ligands
Gou, Shaohua
Ye, Zhongbin
Cai, Xiaoxiao
Liu, Man
Jiang, Wenchao
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (06) : 1136 - 1140
[36] ENANTIOSELECTIVE DEPROTONATION AS A VEHICLE FOR THE ASYMMETRIC-SYNTHESIS OF C-2-SYMMETRICAL P-CHIRAL DIPHOSPHINES
MUCI, AR
CAMPOS, KR
EVANS, DA
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (35) : 9075 - 9076
[37] Enantioselective addition of diethylzinc to aldehydes catalyzed by optically active C2-symmetrical bis-β-amino alcohols
Xu, QY
Zhu, GM
Pan, XF
Chan, ASC
CHIRALITY, 2002, 14 (09) : 716 - 723
[38] Chiral ligands for asymmetric synthesis:: enantioselective addition of diethylzinc to aromatic aldehydes catalyzed by chiral N-α-pyridylmethyl amino alcohols
Yun, HY
Wu, YJ
Wu, YS
Ding, KL
Zhou, Y
TETRAHEDRON LETTERS, 2000, 41 (52) : 10263 - 10266
[39] CHIRAL C-2-SYMMETRICAL 2,5-DISUBSTITUTED PYRROLIDINE DERIVATIVES AS CHIRAL CATALYST LIGANDS IN THE REACTION OF DIETHYLZINE WITH ARYLADLDEHYES
SHI, M
SATOH, Y
MAKIHARA, T
MASAKI, Y
TETRAHEDRON-ASYMMETRY, 1995, 6 (09) : 2109 - 2112
[40] Synthesis of new dendritic chiral BINOL ligands and their applications in enantioselective Lewis acid catalyzed addition of diethylzinc to aldehydes
Fan, QH
Yang, XQ
Liu, GG
Chen, XM
Chan, ASC
CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2003, 24 (02): : 274 - 277

← 1 2 3 4 5 →