Dual Chiral Catalysis Enabled Asymmetric Syntheses of Amines

被引：1

作者：

Xu, Haibo ^{[1
,2
]}

Lin, Zuizhi ^{[1
,2
]}

Bai, Jiahui ^{[1
,2
]}

Guo, Yinlong ^{[1
]}

Ma, Shengming ^{[1
,3
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

[3] Fudan Univ, Res Ctr Mol Recognit & Synth, Dept Chem, Shanghai 200433, Peoples R China

来源：

ACS CATALYSIS | 2023年 / 14卷 / 01期

基金：

国家重点研发计划;

关键词：

dual catalysis; A(3)-coupling reaction; copper; chiralphosphoric acids; chiral counteranion; chiral amines; HIGHLY ENANTIOSELECTIVE SYNTHESIS; BRONSTED ACID; METAL CATALYSIS; PROPARGYLAMINE DERIVATIVES; 3-COMPONENT SYNTHESIS; ACCESS; ACTIVATION; P; N-LIGAND; CONCISE; DESIGN;

D O I：

10.1021/acscatal.3c04269

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：

Due to their importance in natural products, organic synthesis, life science, and pharmaceuticals, reliable methods for the synthesis of chiral amines are urgently required. Here in this contribution, the dual chiral catalytic method has been established for the enantioselective reaction of terminal alkynes, aldehydes, and amines affording optically active propargylic amines with a decent enantioselectivity and a broad substrate scope. These propargylic amines have been demonstrated as platform molecules for the syntheses of different types of chiral amines. By applying this protocol, the asymmetric total syntheses of two linear monoamine natural products, (S)-5 and (S)-11, which were isolated from marine cyanobacteria Microcoleus lyngbyaceus, have been realized. The envisioned chiral ion pair, which has boosted the enantioselectivity greatly, and other key intermediates have been successfully characterized by MS studies.

引用

页码：262 / 270

页数：9

共 67 条

[11] Chiral phosphoric acids: Powerful organocatalysts for asymmetric addition reactions to imines [J].

Connon, Stephen J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (24) :3909-3912

[12] Iterative oxazole assembly via α-chloroglycinates:: Total synthesis of (-)-muscoride A [J].

Coqueron, PY ;

Didier, C ;

Ciufolini, MA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (12) :1411-1414

[13] Acetylenes in catalysis: Enantioselective additions to carbonyl groups and imines and applications beyond [J].

Cozzi, PG ;

Hilgraf, R ;

Zimmermann, N .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (20) :4095-4105

[14] Synthesis of chiral α-aminoalkylpyrimidines using an enantioselective three-component reaction [J].

Dube, H ;

Gommermann, N ;

Knochel, P .

SYNTHESIS-STUTTGART, 2004, (12) :2015-2025

[15] Concise and Diversity-Oriented Route toward Polysubstituted 2-Aminoimidazole Alkaloids and Their Analogues [J].

Ermolat'ev, Denis S. ;

Bariwal, Jitender B. ;

Steenackers, Hans P. L. ;

De Keersmaecker, Sigrid C. J. ;

Van der Eycken, Erik V. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (49) :9465-9468

[16] An easily removable stereo-dictating group for enantioselective synthesis of propargylic amines [J].

Fan, Wu ;

Ma, Shengming .

CHEMICAL COMMUNICATIONS, 2013, 49 (86) :10175-10177

[17] A synthesis of (+)-saxitoxin [J].

Fleming, JJ ;

Du Bois, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (12) :3926-3927

[18] Highly enantioselective synthesis of propargylamines using (mesitylmethyl)benzylamine [J].

Gommermann, N ;

Knochel, P .

SYNLETT, 2005, (18) :2799-2801

[19] Preparation of functionalized primary chiral amines and amides via an enantioselective three-component synthesis of propargylamines [J].

Gommermann, N ;

Knochel, P .

TETRAHEDRON, 2005, 61 (48) :11418-11426

[20] 2-Phenallyl as a versatile protecting group for the asymmetric one-pot three-component synthesis of propargylamines [J].

Gommermann, N ;

Knochel, P .

CHEMICAL COMMUNICATIONS, 2005, (33) :4175-4177

← 1 2 3 4 5 6 7 →