CHIRAL LIGANDS CONTAINING HETEROATOMS .8. 2-[(2S)-2-PYRROLIDINYL]PYRIDINE AS A NOVEL CATALYST IN THE ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES

被引：81

作者：

CHELUCCI, G ^{[1
]}

CONTI, S ^{[1
]}

FALORNI, M ^{[1
]}

GIACOMELLI, G ^{[1
]}

机构：

[1] UNIV SASSARI,DIPARTMENTO CHIM,VIA VIENNA 2,I-07100 SASSARI,ITALY

来源：

TETRAHEDRON | 1991年 / 47卷 / 38期

关键词：

D O I：

10.1016/S0040-4020(01)91018-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title compound has been demonstrated to be an effective enantioselective catalyst in the addition of diethylzinc to aldehydes: optically active secondary alcohols in up to 100% ee were obtained in high yields. The temperature dependence of the stereodynamic course of the reaction was examined and the nature of the possible catalytic complex was discussed on the basis of NMR data too.

引用

页码：8251 / 8258

页数：8

共 50 条

[1] New chiral pyrrolidinyl- and 2-azanorbornyloxazolidine ligands for enantioselective addition of diethylzinc to aldehydes
Nakano, H
Okuyama, Y
Fushimi, K
Yamakawa, R
Kayaoka, D
Hongo, H
HETEROCYCLES, 2002, 56 (1-2) : 457 - 466
[2] METAL-COMPLEXES OF CHIRAL PYRIDINE LIGANDS - X-RAY STRUCTURE OF NITRATOBIS(2-[(2S)-2-PYRROLIDINYL]PYRIDINE)COPPER(II) NITRATE
BACCHI, A
CHELUCCI, G
GRANDINO, M
MINARDI, G
PELIZZI, C
PELIZZI, G
SOLINAS, C
JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 1994, 24 (10) : 659 - 663
[3] 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
[4] SYNTHESIS OF 1-SUBSTITUTED 2-[(2S)-2-PYRROLIDINYL]PYRIDINE FROM L-PROLINE
CHELUCCI, G
FALORNI, M
GIACOMELLI, G
SYNTHESIS-STUTTGART, 1990, (12): : 1121 - 1122
[5] The Enantioselective Addition of Diethylzinc to Aldehydes Catalyzed by 2-Methylquinoline Derived Chiral Ligands
Qian Yong XU
Chinese Chemical Letters, 2001, (05) : 395 - 396
[6] The enantioselective addition of diethylzinc to aldehydes catalyzed by 2-methylquinoline derived chiral ligands
Xu, QY
Wang, GX
Pan, XF
CHINESE CHEMICAL LETTERS, 2001, 12 (05) : 395 - 396
[7] Chiral ligands containing heteroatoms .14. 1,3-oxazolidinyl methanols as chiral catalysts in the enantioselective addition of diethylzinc to aldehydes
Falorni, M
Collu, C
Conti, S
Giacomelli, G
TETRAHEDRON-ASYMMETRY, 1996, 7 (01) : 293 - 299
[8] Chiral ligands containing heteroatoms - XlV. 1,3-Oxazolidinyl methanols as chiral catalysts in the enantioselective addition of diethylzinc to aldehydes
Falorni, M.
Collu, C.
Conti, S.
Giacomelli, G.
Tetrahedron: Asymmetry, 7 (01):
[9] Chiral ligand 2-(2′-piperidinyl)pyridine:: synthesis, resolution and application in asymmetric diethylzinc addition to aldehydes
Cheng, Yan-Qin
Bian, Zheng
Kang, Chuan-Qing
Guo, Hai-Quan
Gao, Lian-Xun
TETRAHEDRON-ASYMMETRY, 2008, 19 (13) : 1572 - 1575
[10] Efficient asymmetric addition of diethylzinc to aldehydes using C2-novel chiral pyridine -amino alcohols as chiral ligands
Zhang, Weijie
Tang, Ruiren
Yu, Huirong
Gao, Shu
APPLIED ORGANOMETALLIC CHEMISTRY, 2014, 28 (07) : 545 - 551

← 1 2 3 4 5 →