Catalytic enantioselective alkyl and aryl addition to aldehydes and ketones with organozinc reagents derived from alkyl Grignard reagents or arylboronic acids

被引：52

作者：

Hatano, Manabu ^{[1
]}

Gouzu, Riku ^{[2
]}

Mizuno, Tomokazu ^{[1
]}

Abe, Hitoshi ^{[2
]}

Yamada, Toshihide ^{[2
]}

Ishihara, Kazuaki ^{[1
,3
]}

机构：

[1] Nagoya Univ, Grad Sch Engn, Chikusa Ku, Nagoya, Aichi 4648603, Japan

[2] Sekisui Med Co Ltd, Hachimantai, Iwate 0287305, Japan

[3] Japan Sci & Technol Agcy JST, CREST, Chikusa Ku, Nagoya, Aichi 4648603, Japan

来源：

CATALYSIS SCIENCE & TECHNOLOGY | 2011年 / 1卷 / 07期

关键词：

CHIRAL SECONDARY ALCOHOLS; GREEN CHEMISTRY APPROACH; ASYMMETRIC-SYNTHESIS; ALLYLIC ALCOHOLS; DIORGANOZINC COMPOUNDS; DIALKYLZINC ADDITION; ENANTIOMERIC EXCESS; RECENT PROGRESS; PHENYL TRANSFER; BASE CATALYSTS;

D O I：

10.1039/c1cy00108f

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A highly practical, catalytic enantioselective alkyl and aryl addition to aldehydes and ketones with organozinc reagents, which were prepared in situ from commercially available Grignard reagents or arylboronic acids, was developed. A chiral phosphoramide ligand was essential for promoting the addition reactions in high yields with high enantioselectivities.

引用

页码：1149 / 1158

页数：10

共 50 条

[21] Catalytic enantioselective addition of organoaluminum reagents to aldehydes
Fernandez-Mateos, Emilio
Macia, Beatriz
Yus, Miguel
[J]. TETRAHEDRON-ASYMMETRY, 2012, 23 (10) : 789 - 794
[22] 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):
[23] CONJUGATE ADDITION OF ALKYL-GRIGNARD REAGENTS TO MONONITROARENES
BARTOLI, G
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1984, 17 (03) : 109 - 115
[24] NATURE OF ALKYL TRANSFER IN REACTIONS OF GRIGNARD-REAGENTS WITH KETONES
ASHBY, EC
BOWERS, JS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (26) : 8504 - 8505
[25] 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
[26] Iron nanoparticles in the coupling of alkyl halides with aryl Grignard reagents
Bedford, RB
Betham, M
Bruce, DW
Davis, SA
Frost, RM
Hird, M
[J]. CHEMICAL COMMUNICATIONS, 2006, (13) : 1398 - 1400
[27] CHARACTERIZATION OF ALKYL AND ARYL HALIDES BY 2,4-DINITROPHENYLHYDRAZONES OF ALDEHYDES FROM REACTION OF THEIR GRIGNARD REAGENTS WITH DIMETTHYLFORMAMIDE
SHAREFKIN, JG
FORSCHIRM, A
[J]. ANALYTICAL CHEMISTRY, 1963, 35 (11) : 1616 - &
[28] STEREOCHEMISTRY OF ADDITION OF GRIGNARD REAGENTS TO 2-ALKYL-CYCLOHEXANONES
MAUJEAN, A
FICINI, J
[J]. BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1970, (11B): : 86 - &
[29] Catalytic Enantioselective Addition of Alkylzirconium Reagents to Aliphatic Aldehydes
Vaccari, Jade
Gonzalez-Soria, Maria Jose
Carter, Nicholas
Macia, Beatriz
[J]. MOLECULES, 2021, 26 (15):
[30] Catalytic enantioselective addition of Grignard reagents to aromatic silyl ketimines
Jiawei Rong
Juan F. Collados
Pablo Ortiz
Ravindra P. Jumde
Edwin Otten
Syuzanna R. Harutyunyan
[J]. Nature Communications, 7

← 1 2 3 4 5 →