N -Triflylphosphorimidoyl Trichloride: A Versatile Reagent for the Synthesis of Strong Chiral BrOnsted Acids

被引：15

作者：

Lee, Sunggi ^{[1
]}

Kaib, Philip S. J. ^{[1
]}

List, Benjamin ^{[1
]}

机构：

[1] Max Planck Inst Kohlenforsch, Kaiser Wilhelm Pl 1, D-45470 Mulheim, Germany

来源：

SYNLETT | 2017年 / 28卷 / 12期

基金：

欧洲研究理事会;

关键词：

N-triflylphosphorimidoyl trichloride; BrOnsted acid; N-triflylphosphoramide; N-triflylthiophosphoramide; N; N-bis(triflyl)phosphoramidimidate; DIELS-ALDER REACTION; MUKAIYAMA ALDOL REACTION; FRIEDEL-CRAFTS REACTION; PHOSPHORIC-ACID; ENANTIOSELECTIVE SYNTHESIS; TRIFLYL PHOSPHORAMIDE; ASYMMETRIC CATALYSIS; INDOLE-DERIVATIVES; CALCIUM-PHOSPHATE; HYDROSILOXYLATION;

D O I：

10.1055/s-0036-1588782

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of strong Bronsted acids has been synthesized in high yields using N- triflylphosphorimidoyl trichloride as reagent. The syntheses proceed efficiently with electron- rich, electron- deficient, and sterically hindered substrates.

引用

页码：1478 / 1480

页数：3

共 49 条

[1] Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid [J].

Akiyama, T ;

Itoh, J ;

Yokota, K ;

Fuchibe, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) :1566-1568

[2] Stronger bronsted acids [J].

Akiyama, Takahiko .

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

[3] Stronger Bronsted Acids: Recent Progress [J].

Akiyama, Takahiko ;

Mori, Keiji .

CHEMICAL REVIEWS, 2015, 115 (17) :9277-9306

[4] Chiral Bronsted acid-catalyzed enantioselective ionic [2+4] cycloadditions [J].

Borovika, Alina ;

Nagorny, Pavel .

TETRAHEDRON, 2013, 69 (27-28) :5719-5725

[5] A Bronsted acid catalyst for the enantioselective protonation reaction [J].

Cheon, Cheol Hong ;

Yamamoto, Hisashi .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) :9246-+

[6] N-Triflylthiophosphoramide Catalyzed Enantioselective Mukaiyama Aldol Reaction of Aldehydes with Silyl Enol Ethers of Ketones [J].

Cheon, Cheol Hong ;

Yamamoto, Hisashi .

ORGANIC LETTERS, 2010, 12 (11) :2476-2479

[7] Bimolecular coupling reactions through oxidatively generated aromatic cations: scope and stereocontrol [J].

Cui, Yubo ;

Villafane, Louis A. ;

Clausen, Dane J. ;

Floreancig, Paul E. .

TETRAHEDRON, 2013, 69 (36) :7618-7626

[8] Asymmetric Bronsted acid catalyzed isoindoline synthesis: Enhancement of enantiomeric ratio by stereoablative kinetic resolution [J].

Enders, Dieter ;

Narine, Arun A. ;

Toulgoat, Fabien ;

Bisschops, Tom .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (30) :5661-5665

[9] Asymmetric organocatalytic reduction of ketimines with catecholborane employing a N-triflyl phosphoramide Bronsted acid as catalyst [J].

Enders, Dieter ;

Rembiak, Andreas ;

Seppelt, Matthias .

TETRAHEDRON LETTERS, 2013, 54 (06) :470-473

[10] Enantioselective Organocatalytic Synthesis of Arylglycines via Friedel-Crafts Alkylation of Arenes with a Glyoxylate Imine [J].

Enders, Dieter ;

Seppelt, Matthias ;

Beck, Tobias .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (09) :1413-1418

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