Catalytic Enantioselective Synthesis of Diarylmethanols from Aryl Bromides and Aldehydes by Using Organolithium Reagents

被引：28

作者：

Nakagawa, Yuya ^{[1
]}

Muramatsu, Yusuke ^{[1
]}

Harada, Toshiro ^{[1
]}

机构：

[1] Kyoto Inst Technol, Dept Chem & Mat Technol, Sakyo Ku, Kyoto 6068585, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 34期

关键词：

Alcohols; Aldehydes; Asymmetric catalysis; Lithium; Titanium; ASYMMETRIC ARYLATION; GRIGNARD-REAGENTS; BORONIC ACIDS; ALKYLATION; KETONES;

D O I：

10.1002/ejoc.201001254

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general method has been developed for preparing enantio-enriched secondary alcohols by starting from aryl bromides and aldehydes. Aryl bromides were first treated with BuLi, and the resulting aryllithium reagents were mixed with titanium tetraisopropoxide and magnesium bromide. The reaction of aldehydes with the resulting mixed titanium reagents, in the presence of 3-(3,5-diphenylphenyl)-H-8-BINOL (2 mol-%) and titanium tetraisopropoxide, furnished the corresponding alcohols in high enantioselectivities and in high yields.

引用

页码：6535 / 6538

页数：4

共 50 条

[1] Catalytic Enantioselective Arylation of Aldehydes by Using Functionalized Grignard Reagents Generated from Aryl Bromides
Itakura, Daisuke
Harada, Toshiro
[J]. SYNLETT, 2011, (19) : 2875 - 2879
[2] Functionalized organolithium reagents in the synthesis of chiral ligands for catalytic enantioselective addition of diethylzinc to aldehydes
Dobrikov, Georgi M.
Philipova, Irena
Nikolova, Rositsa
Shivachev, Boris
Chimov, Angel
Dimitrov, Vladimir
[J]. POLYHEDRON, 2012, 45 (01) : 126 - 143
[3] Asymmetric, catalytic phenyl transfer to aldehydes:: Enantioselective synthesis of diarylmethanols
Bolm, C
Hermanns, N
Hildebrand, JP
Muñiz, K
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2000, 39 (19) : 3465 - +
[4] Catalytic Asymmetric Addition of Organolithium Reagents to Aldehydes
Veguillas, Marcos
Sola, Ricard
Shaw, Luke
Macia, Beatriz
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (09) : 1788 - 1794
[5] Catalytic Enantioselective Alkylation of Aldehydes by Using Organozinc Halide Reagents
Kinoshita, Yuichiro
Kanehira, Shinichi
Hayashi, Yasuki
Harada, Toshiro
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (10) : 3311 - 3314
[6] Catalytic Enantioselective Alkylation and Arylation of Aldehydes by Using Grignard Reagents
Muramatsu, Yusuke
Kanehira, Shinichi
Tanigawa, Masato
Miyawaki, Yuta
Harada, Toshiro
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2010, 83 (01) : 19 - 32
[7] Aryl Bromides as Inexpensive Starting Materials in the Catalytic Enantioselective Arylation of Aryl Aldehydes: The Additive TMEDA Enhances the Enantioselectivity
Yang, Yong-Xin
Liu, Yue
Zhang, Lei
Jia, Yan-E
Wang, Pei
Zhuo, Fang-Fang
An, Xian-Tao
Da, Chao-Shan
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (21): : 10696 - 10702
[8] Catalytic enantioselective alkyl and aryl addition to aldehydes and ketones with organozinc reagents derived from alkyl Grignard reagents or arylboronic acids
Hatano, Manabu
Gouzu, Riku
Mizuno, Tomokazu
Abe, Hitoshi
Yamada, Toshihide
Ishihara, Kazuaki
[J]. CATALYSIS SCIENCE & TECHNOLOGY, 2011, 1 (07) : 1149 - 1158
[9] Catalytic Enantioselective Addition of Organozirconium Reagents to Aldehydes
Sola, Ricard
Veguillas, Marcos
Gonzalez-Soria, Maria Jose
Carter, Nicholas
Fernandez-Ibanez, M. Angeles
Macia, Beatriz
[J]. MOLECULES, 2018, 23 (04):
[10] Catalytic enantioselective addition of organoaluminum reagents to aldehydes
Fernandez-Mateos, Emilio
Macia, Beatriz
Yus, Miguel
[J]. TETRAHEDRON-ASYMMETRY, 2012, 23 (10) : 789 - 794

← 1 2 3 4 5 →