Asymmetric Addition of Diethyl Zinc to Benzaldehyde Catalyzed by Chiral Diamine Ligand and Ti-diamine Modified Complex Derived from D-mannitol

被引：0

作者：

Al Majid, Abdullah M. A. ^{[1
]}

Al-Hazimi, Hassan M. A. ^{[1
]}

Al-Shammery, Mohammed B. ^{[2
]}

机构：

[1] King Saud Univ, Fac Sci, Chem Dept, POB 2455, Riyadh 11451, Saudi Arabia

[2] Alkharj Univ, Fac Sci & Humanitarian Studies, Alkharj, Saudi Arabia

来源：

JORDAN JOURNAL OF CHEMISTRY | 2010年 / 5卷 / 03期

关键词：

Diazide; Chiral diamine; Ttitanium complex; Diethyl zinc; Benzaldehyde; Asymmetric; Enantioselectivity; Addition;

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Modified procedure for preparation of chiral: 3,4-Diazido-1, 2:5, 6-di-O-isopropylidene-Dmannitol from the corresponding bismesylate and new chiral ligand: 3, 4-diamino-1, 2:5, 6-Oisopropylidene-D-mannitol was described. The application of both diamine and Ti-diamine complex as catalysts in enantioselective addition of diethyl zinc to prochiral benzaldehyde was described. High enantioselectivity up to 93% e.e. was achieved. The standard analytical measurements including optical activity of the diazide, diamine and the determination of optical purity of the resulting alcohol were reported. [GRAPHICS]

引用

页码：221 / 230

页数：10

共 37 条

[1] Al-Majid A. M., 2003, J SAUDI CHEM SOC, V7, P65
[2] Al-Majid A. M., 1998, J SAUDI CHEM SOC, V2, P67
[3] Al-Majid A. M., 2010, J SAUDI CHEM SOC, P14
[4] CHIRAL 1,2-DIPHOSPHINE LIGANDS - SYNTHESIS AND APPLICATION TO RHODIUM-CATALYZED ASYMMETRIC HYDROGENATIONS
AMMA, JP
STILLE, JK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (03) : 468 - 473
[5] [Anonymous], 1994, ASYMMETRIC CATALYSIS
[6] Practical asymmetric henry reaction catalyzed by a chiral Diamine-Cu(OAc)2 complex
Arai, Takayoshi
Watanabe, Masahiko
Yanagisawa, Akira
[J]. ORGANIC LETTERS, 2007, 9 (18) : 3595 - 3597
[7] Reaction of azides with dichloroindium hydride: Very mild production of amines and pyrrolidin-2-imines through possible indium-aminyl radicals
Benati, Luisa
Bencivenni, Giorgio
Leardini, Rino
Nanni, Daniele
Minozzi, Matteo
Spagnolo, Piero
Scialpi, Rosanna
Zanardi, Giuseppe
[J]. ORGANIC LETTERS, 2006, 8 (12) : 2499 - 2502
[8] Introduction: Enantioselective catalysis
Bolm, C
Gladysz, JA
[J]. CHEMICAL REVIEWS, 2003, 103 (08) : 2761 - 2762
[9] Organic azides:: An exploding diversity of a unique class of compounds
Bräse, S
Gil, C
Knepper, K
Zimmermann, V
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) : 5188 - 5240
[10] Preparation of 3-amino-1,4-benzodiazepin-2-ones via direct azidation with trisyl azide
Butcher, JW
Liverton, NJ
Selnick, HG
Elliot, JM
Smith, GR
Tebben, AJ
Pribush, DA
Wai, JS
Claremon, DA
[J]. TETRAHEDRON LETTERS, 1996, 37 (37) : 6685 - 6688

← 1 2 3 4 →