Direct Asymmetric Aldol Reaction of Acetophenones and Aromatic Aldehydes Catalyzed by Chiral Al/Zn Heterobimetallic Compounds ZABDP

被引：0

作者：

Li Xiao ^{[1
,2
]}

Gao Liguo ^{[1
]}

Gong Ying ^{[1
]}

Ma Yajun ^{[1
]}

Ma Xiangrong ^{[1
]}

机构：

[1] Yulin Univ, Sch Chem & Chem Engn, Yulin 719000, Peoples R China

[2] Lanzhou Univ, Inst Biochem & Mol Biol, Sch Life Sci, Lanzhou 730000, Peoples R China

来源：

CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE | 2017年 / 38卷 / 05期

基金：

中国国家自然科学基金;

关键词：

Asymmetric synthesis; Asymmetric catalysis; Heterobimetallic; Aldol reaction; Acetophenone; SEMI-CROWN LIGANDS; GALLIUM LEWIS-ACID; BASE COMPLEX; KETONES; PROLINE; MICHAEL; MANNICH;

D O I：

10.7503/cjcu20160752

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A chiral Al/Zn heterobimetallic complex,(R,S,S)-3,3'-bis[(N-diphenylprolinol) methyl] -2,2'-bis-(methoxymethyl)-1,1'-binaphthol Al/Zn heterobimetallic complex(ZABDP) was designed as catalyst, to catalyze the direct asymmetric Aldol reaction of acetophenones and aromatic aldehydes. The Al center acts as a Lewis acid to activate the aldehydes while ethylzinc alkoxide functions as a Bronsted base to form the reactive zinc enolates in the complex ZABDP. The distinct actors of the two different metals contribute to the efficient direct asymmetric Aldol reaction, the highest e.e. value is 90% and yield is 99%

引用

页码：778 / 785

页数：8

共 39 条

[1] Alcaide B, 2002, EUR J ORG CHEM, V2002, P1595
[2] The vinylogous aldol reaction: A valuable, yet understated carbon-carbon bond-forming maneuver
Casiraghi, G
Zanardi, F
Appendino, G
Rassu, G
[J]. CHEMICAL REVIEWS, 2000, 100 (06) : 1929 - 1972
[3] Lewis base activation of Lewis acids. Catalytic enantioselective addition of silyl enol ethers of achiral methyl ketones to aldehydes
Denmark, SE
Heemstra, JR
[J]. ORGANIC LETTERS, 2003, 5 (13) : 2303 - 2306
[4] A tandem enol silane formation-Mukaiyama aldol reaction mediated by TMSOTf
Downey, C. Wade
Johnson, Miles W.
[J]. TETRAHEDRON LETTERS, 2007, 48 (20) : 3559 - 3562
[5] Heterobimetallic Transition Metal/Rare Earth Metal Bifunctional Catalysis: A Cu/Sm/Schiff Base Complex for Syn-Selective Catalytic Asymmetric Nitro-Mannich Reaction
Handa, Shinya
Gnanadesikan, Vijay
Matsunaga, Shigeki
Shibasaki, Masakatsu
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (13) : 4925 - 4934
[6] Direct Catalytic Enantio- and Diastereoselective Aldol Reaction of Thioamides
Iwata, Mitsutaka
Yazaki, Ryo
Chen, I-Hon
Sureshkumar, Devarajulu
Kumagai, Naoya
Shibasaki, Masakatsu
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (14) : 5554 - 5560
[7] Chiral bis(oxazoline) copper(II) complexes: Versatile catalysts for enantioselective cycloaddition, aldol, Michael, and carbonyl ene reactions
Johnson, JS
Evans, DA
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) : 325 - 335
[8] Dicationic ((-)-sparteine)palladium-catalyzed enantioselective aldol reaction of aldehydes with 1-phenyl-1-trimethylsilyloxyethene, proceeding via a palladium enolate
Kiyooka, Syun-ichi
Takeshita, Yushi
Tanaka, Yoshinori
Higaki, Takafumi
Wada, Yosuke
[J]. TETRAHEDRON LETTERS, 2006, 47 (26) : 4453 - 4456
[9] Direct catalytic enantio- and diastereoselective aldol reaction using a Zn-Zn-linked-BINOL complex:: A practical synthesis of syn-1,2-diols
Kumagai, N
Matsunaga, S
Yoshikawa, N
Ohshima, T
Shibasaki, M
[J]. ORGANIC LETTERS, 2001, 3 (10) : 1539 - 1542
[10] Li GW, 2012, PROG CHEM, V24, P348

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