Quinine-Catalyzed Asymmetric Synthesis of 2,2′-Binaphthol-Type Biaryls under Mild Reaction Conditions

被引：121

作者：

Moliterno, Mauro ^{[1
]}

Cari, Riccardo ^{[1
]}

Puglisi, Antonio ^{[1
]}

Antenucci, Achille ^{[1
]}

Sperandio, Celine ^{[1
]}

Moretti, Erica ^{[1
]}

Di Sabato, Antonio ^{[1
]}

Salvio, Riccardo ^{[1
,2
]}

Bella, Marco ^{[1
]}

机构：

[1] Univ Roma La Sapienza, Dipartimento Chim, Ple Aldo Moro 5, I-00185 Rome, Italy

[2] Univ Roma La Sapienza, IMC CNR Sez Meccanismi Reaz, Ple Aldo Moro 5, I-00185 Rome, Italy

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 22期

关键词：

atropisomers; biaryls; chirality; density-functional calculations; organocatalysis; ENANTIOSELECTIVE SYNTHESIS; ALPHA-ARYLATION; ATROPISOMERS; DERIVATIVES; LIGANDS; BINOL; BROMINATION; RESOLUTION; COMPLEXES; NAPHTHOLS;

D O I：

10.1002/anie.201601660

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Simple quinine as an organocatalyst mediates the addition of various naphthols to halogenated quinones to afford non-C-2-symmetrical, axially chiral biaryl products, which are promising compounds as chiral ligands and organocatalysts. The rotational barrier required to have two distinct atropisomers has been evaluated in the products generated from the addition of naphthols to various quinones by means of DFT calculations and HPLC. The use of halogenated quinones as reagents was necessary to have configurationally stable enantiomeric products which can be obtained in good yield and stereoselectivity. These compounds have also been prepared in gram quantities and recrystallized to near enantiopurity.

引用

页码：6525 / 6529

页数：5

共 43 条

[1] Scalable Synthesis of Enantiomerically Pure Bicyclo[2.2.2]octadiene Ligands [J].

Abele, Stefan ;

Inauen, Roman ;

Spielvogel, Dirk ;

Moessner, Christian .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (10) :4765-4773

[2]

Adair G, 2008, ALDRICHIM ACTA, V41, P31

[3] Stronger bronsted acids [J].

Akiyama, Takahiko .

CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758

[4]

Aleman J., 2007, ANGEW CHEM, V119, P5611

[5]

Aleman J., 2007, Angew. Chem. Int. Ed, V119, P5616

[6] Asymmetric organocatalytic α-arylation of aldehydes [J].

Aleman, Jose ;

Cabrera, Silvia ;

Maerten, Eddy ;

Overgaard, Jacob ;

Jorgensen, Karl Anker .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) :5520-5523

[7] Organocatalytic highly enantioselective α-arylation of β-ketoesters [J].

Aleman, Jose ;

Richter, Bo ;

Jorgensen, Karl Anker .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) :5515-5519

[8]

[Anonymous], 2010, CATALYTIC ASYMMETRIC

[9] Synergic asymmetric organocatalysis (SAOc) of Cinchona alkaloids and secondary amines in the synthesis of bicyclo[2.2.2]octan-2-ones [J].

Bella, Marco ;

Schietroma, Daniele M. Scarpino ;

Cusella, Pier Paolo ;

Gasperi, Tecla ;

Visca, Valerio .

CHEMICAL COMMUNICATIONS, 2009, (05) :597-599

[10] Organocatalytic Strategies for the Synthesis of Axially Chiral Compounds [J].

Bencivenni, Giorgio .

SYNLETT, 2015, 26 (14) :1915-1922

← 1 2 3 4 5 →