Chiral Arylaminophosphonium Barfates as a New Class of Charged Bronsted Acid for the Enantioselective Activation of Nonionic Lewis Bases

被引：98

作者：

Uraguchi, Daisuke ^{[1
]}

Nakashima, Daisuke ^{[1
]}

Ooi, Takashi ^{[1
]}

机构：

[1] Nagoya Univ, Dept Appl Chem, Grad Sch Engn, Nagoya, Aichi 4648603, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 21期

关键词：

DIELS-ALDER REACTION; PROTON CATALYSIS; 1,3-DICARBONYL COMPOUNDS; MICHAEL ADDITION; GUANIDINE; AZA; NITROALKENES; THIOUREAS; LIGANDS; INDOLES;

D O I：

10.1021/ja903271t

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Heterochiral [7.7]-P-spirocyclic arylaminophosphonium barfates have been designed as a novel charged, cationic Bronsted acid catalyst, and their catalytic and stereocontrolting abilities have been clearly demonstrated in the development of the unprecedented, highly enantioselective conjugate addition of arylamines to nitroolefins. This study uncovers a new function of chiral tetraaminophosphonium cations and its potential synthetic utility, thereby providing a new avenue to the molecular design of chiral charged Bronsted acid catalysts and their applications.

引用

页码：7242 / +

页数：3

共 41 条

[1] Enantioselective Bromocycloetherification by Lewis Base/Chiral Bronsted Acid Cooperative Catalysis
Denmark, Scott E.
Burk, Matthew T.
ORGANIC LETTERS, 2012, 14 (01) : 256 - 259
[2] Titanium tetrachloride and chiral aliphatic alcohol as a new Lewis acid assisted chiral Bronsted acid for the enantioselective protonation of silyl enol ether
Nakashima, D
Yamamoto, H
SYNLETT, 2006, (01) : 150 - 152
[3] Enantioselective Addition of Boronates to Chromene Acetals Catalyzed by a Chiral Bronsted Acid/Lewis Acid System
Moquist, Philip N.
Kodama, Tomohiro
Schaus, Scott E.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (39) : 7096 - 7100
[4] First enantioselective protonation of prochiral allyltrimethyltins using Lewis acid assisted chiral bronsted acids
Ishihara, K
Ishida, Y
Nakamura, S
Yamamoto, H
SYNLETT, 1997, (07) : 758 - +
[5] Tin(IV) chloride-chiral pyrogallol derivatives as new lewis acid-assisted chiral bronsted acids for enantioselective polyene cyclization
Kumazawa, K
Ishihara, K
Yamamoto, H
ORGANIC LETTERS, 2004, 6 (15) : 2551 - 2554
[6] New developments in enantioselective Bronsted acid catalysis - Chiral ion pair catalysis
Rueping, Magnus
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2007, 50 (13-14): : 1279 - 1280
[7] Development and Mechanism of an Enantioselective Bromocycloetherification Reaction via Lewis Base/Chiral BrOnsted Acid Cooperative Catalysis
Denmark, Scott E.
Burk, Matthew T.
CHIRALITY, 2014, 26 (07) : 344 - 355
[8] Application of Chiral Lewis Base/Bronsted Acid Synergistic Catalysis Strategy in Enantioselective Synthesis of Organic Sulfides
Zhu Deng
Chen Zhi-Min
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (10) : 3015 - 3032
[9] The crystallographic structure of a Lewis acid-assisted chiral Bronsted acid as an enantioselective protonation reagent for silyl enol ethers
Yamamoto, H. (yamamoto@uchicago.edu), 1600, American Chemical Society (125):
[10] The crystallographic structure of a Lewis acid-assisted chiral Bronsted acid as an enantioselective protonation reagent for silyl enol ethers
Ishihara, K
Nakashima, D
Hiraiwa, Y
Yamamoto, H
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (01) : 24 - 25

← 1 2 3 4 5 →