Enantioselective addition of Et2Zn to aldehydes catalyzed by chiral aliphatic β-amino alcohols

被引：0

作者：

Shen, ZX ^{[1
]}

Xu, XN ^{[1
]}

Liu, XF ^{[1
]}

Zhang, LF ^{[1
]}

Zhang, YW ^{[1
]}

机构：

[1] Suzhou Univ, Dept Chem & Chem Engn, Suzhou 215006, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2000年 / 18卷 / 04期

关键词：

enantioselective addition; beta-amino alcohol; enantioselectivity;

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This paper describes the preparation of two new optically active aliphatic beta-amino alcohols (R)-5,5-dimethyl-2(dimethylamino)-1,1-diphenyl-1-hexanol (1a) and (S)-8,8-dimethyl-2-(dimethylamino)-1,1-diphenyl-1-nonanol (Ib). They were synthesized by methylation of the corresponding beta-amino alcohols 2a and 2b. Compounds la and Ib catalyze the addition of diethylzinc to various aldehydes enantioselectively. The catalyst structure-enantioselectivity relationships were discussed.

引用

页码：582 / 584

页数：3

共 50 条

[11] ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES CATALYZED BY SECONDARY AMINO-ALCOHOLS
TANAKA, K
USHIO, H
SUZUKI, H
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (22) : 1700 - 1701
[12] Enantioselective addition of diethylzinc to aldehydes catalyzed by chiral amino alcohols. Substituent effect and nonlinear effect
Ohga, T
Umeda, S
Kawanami, Y
TETRAHEDRON, 2001, 57 (23) : 4825 - 4829
[13] ENANTIOSELECTIVE ADDITION OF DIORGANOZINCS TO ALDEHYDES CATALYZED BY BETA-AMINO ALCOHOLS
NOYORI, R
SUGA, S
KAWAI, K
OKADA, S
KITAMURA, M
OGUNI, N
HAYASHI, M
KANEKO, T
MATSUDA, Y
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 382 (1-2) : 19 - 37
[14] 3,3′-Dipyridyl BINOL ligands.: Synthesis and application in enantioselective addition of Et2Zn to aldehydes
Milburn, Robert R.
Hussain, S. M. Shakil
Prien, Olaf
Ahmed, Zaheer
Snieckus, Victor
ORGANIC LETTERS, 2007, 9 (22) : 4403 - 4406
[15] Nickel complexes from α-amino amides as efficient catalysts for the enantioselective Et2Zn addition to benzaldehyde
Burguete, MI
Collado, M
Escorihuela, J
Galindo, F
García-Verdugo, E
Luis, SV
Vicent, MJ
TETRAHEDRON LETTERS, 2003, 44 (36) : 6891 - 6894
[16] Enantioselective Addition of Diethylzinc to Aromatic Aldehydes Catalyzed by Pyrolidine and Piperidine -Amino Alcohols
Salehi, Peyman
Dabiri, Minoo
Kozehgary, Gholamreza
Heydari, Seddigheh
SYNTHETIC COMMUNICATIONS, 2009, 39 (14) : 2575 - 2584
[17] 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
[18] Enantioselective addition of diethylzinc to aldehydes catalyzed by γ-amino alcohols derived from (+)- and (-)-α-pinene
Szakonyi, Z
Balázs, A
Martinek, TA
Fülöp, F
TETRAHEDRON-ASYMMETRY, 2006, 17 (02) : 199 - 204
[19] Highly Enantioselective Addition of Terminal Alkynes to Aldehydes Catalyzed by a New Chiral β-Sulfonamide Alcohol/Ti(OiPr)4/Et2Zn/R3N Catalyst System
Qiu, Li
Wang, Quan
Lin, Li
Liu, Xiaodong
Jiang, Xianxing
Zhao, Qingyang
Hu, Guowen
Wang, Rui
CHIRALITY, 2009, 21 (02) : 316 - 323
[20] Modular amino alcohol ligands containing bulky alkyl groups as chiral controllers for Et2Zn addition to aldehydes:: Illustration of a design principle
Jimeno, C
Pastó, M
Riera, A
Pericàs, MA
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (08): : 3130 - 3138

← 1 2 3 4 5 →