Bi(OTf)3-Catalyzed Diastereoselective One-Pot Synthesis of 1,3-Diamines with Three Continuous Stereogenic Centers

被引：14

作者：

Halli, Juliette ^{[1
]}

Kramer, Philipp ^{[3
]}

Grimmer, Jennifer ^{[3
]}

Bolte, Michael ^{[2
]}

Manolikakes, Georg ^{[3
]}

机构：

[1] Goethe Univ Frankfurt Main, Inst Organ Chem & Chem Biol, Max von Laue Str 7, D-60438 Frankfurt, Germany

[2] Goethe Univ Frankfurt Main, Inst Inorgan & Analyt Chem, Max von Laue Str 7, D-60438 Frankfurt, Germany

[3] Tech Univ Kaiserslautern, Inst Organ Chem, Erwin Schrodinger Str Geb 54, D-67663 Kaiserslautern, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 19期

关键词：

AMINO-ACID DERIVATIVES; STEREODIVERGENT SYNTHESIS; 3-COMPONENT SYNTHESIS; BRONSTED ACID; TRIFLIC ACID; CATALYSIS; ENAMIDES; IMINES; ORGANOCATALYSIS; NUCLEOPHILES;

D O I：

10.1021/acs.joc.8b01925

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly modular, diastereoselective one-pot-synthesis of 1,3-diamines with three contiguous stereogenic centers is reported. Our method provides a fast and efficient access to 1,2-anti-2,3-anti-1,3-diamines from three readily available building blocks. This Bi(OTf)(3)-catalyzed reaction is insensitive to air and moisture and can be performed on a multigram scale.

引用

页码：12007 / 12022

页数：16

共 51 条

[21] Imine and iminium precursors as versatile intermediates in enantioselective organocatalysis [J].

Kataja, Antti O. ;

Masson, Geraldine .

TETRAHEDRON, 2014, 70 (46) :8783-8815

[22] MANZACIDINS AC, NOVEL TETRAHYDROPYRIMIDINE ALKALOIDS FROM THE OKINAWAN MARINE SPONGE HYMENIACIDON SP [J].

KOBAYASHI, J ;

KANDA, F ;

ISHIBASHI, M ;

SHIGEMORI, H .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (14) :4574-4576

[23] Stereoselective One-Pot Synthesis of Dihydropyrimido[2,1-a]isoindole-6(2H)-ones [J].

Kramer, Philipp ;

Schoenfeld, Julia ;

Bolte, Michael ;

Manolikakes, Georg .

ORGANIC LETTERS, 2018, 20 (01) :178-181

[24] Synthesis and crystal structures of two structurally related kryptoracemates [J].

Kramer, Philipp ;

Bolte, Michael .

ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2017, 73 :575-581

[25] Synthesis of 1,3-Diamines Through Rhodium-Catalyzed C-H Insertion [J].

Kurokawa, Toshiki ;

Kim, Mihyong ;

Du Bois, J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (15) :2777-2779

[26] Enantioselective Aminomethylamination of Conjugated Dienes with Aminals Enabled by Chiral Palladium Complex-Catalyzed C-N Bond Activation [J].

Liu, Yang ;

Xie, Yinjun ;

Wang, Hongli ;

Huang, Hanmin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (13) :4314-4317

[27] Cyclizations of N-acyliminium ions [J].

Maryanoff, BE ;

Zhang, HC ;

Cohen, JH ;

Turchi, IJ ;

Maryanoff, CA .

CHEMICAL REVIEWS, 2004, 104 (03) :1431-1628

[28] Copper(II)-catalyzed highly enantioselective addition of enamides to imines: The use of enamides as nucleophiles in asymmetric catalysis [J].

Matsubara, R ;

Nakamura, Y ;

Kobayashi, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (13) :1679-1681

[29] Enamides and enecarbamates as nucleophiles in stereoselective C-C and C-N bond-forming reactions [J].

Matsubara, Ryosuke ;

Kobayashi, Shu .

ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (02) :292-301

[30] Molecular basis of human immunodeficiency virus type 1 drug resistance: Overview and recent developments [J].

Menendez-Arias, Luis .

ANTIVIRAL RESEARCH, 2013, 98 (01) :93-120

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