Highly Enantioselective Intermolecular Hydroamination of Allylic Amines with Chiral Aldehydes as Tethering Catalysts

被引：60

作者：

MacDonald, Melissa J. ^{[1
]}

Hesp, Colin R. ^{[1
]}

Schipper, Derek J. ^{[1
]}

Pesant, Marc ^{[2
]}

Beauchemin, Andre M. ^{[1
]}

机构：

[1] Univ Ottawa, Dept Chem, Ctr Catalysis Res & Innovat, Ottawa, ON K1N 6N5, Canada

[2] Boehringer Ingelheim Canada Ltd, Laval, PQ H7S 2G5, Canada

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 08期

基金：

加拿大自然科学与工程研究理事会;

关键词：

asymmetric catalysis; hydroamination; hydroxylamines; tethered reactions; vicinal diamines; COPE-TYPE HYDROAMINATION; HYDROXYL-DIRECTED METHANOLYSIS; ASYMMETRIC HYDROAMINATION; INDUCED INTRAMOLECULARITY; ALPHA-AMINONITRILES; CARBONYL-COMPOUNDS; STRECKER SYSTEMS; ALKENES; STRATEGY; ALLYLAMINES;

D O I：

10.1002/chem.201203462

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chirally LinkedIn: Chiral aldehydes are effective tethering catalysts for enantioselective intermolecular hydroamination, which provides access to vicinal diamine motifs in good yields and excellent enantioselectivities (see scheme). This work highlights simple chiral α-oxygenated aldehydes as effective organocatalysts capable of efficiently inducing asymmetry through transient intramolecularity. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：2597 / 2601

页数：5

共 50 条

[21] CHIRAL OXAZABOROLIDINES AS CATALYSTS FOR THE ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES
JOSHI, NN
SREBNIK, M
BROWN, HC
TETRAHEDRON LETTERS, 1989, 30 (41) : 5551 - 5554
[22] CHIRAL CATALYSTS FOR THE ENANTIOSELECTIVE ADDITION OF ORGANOMETALLIC REAGENTS TO ALDEHYDES
COREY, EJ
HANNON, FJ
TETRAHEDRON LETTERS, 1987, 28 (44) : 5233 - 5236
[23] Enantioselective alkynylation of aldehydes catalyzed by new chiral catalysts
Chan, ASC
Lu, G
Li, XS
METHODOLOGIES IN ASYMMETRIC CATALYSIS, 2004, 880 : 103 - 113
[24] Ir(I)-Catalyzed Intermolecular Regio- and Enantioselective Hydroamination of Alkenes with Heteroaromatic Amines
Pan, Shiguang
Endo, Kohei
Shibata, Takanori
ORGANIC LETTERS, 2012, 14 (03) : 780 - 783
[25] Highly enantioselective addition of dialkylzincs to aldehydes using dendritic chiral catalysts with flexible carbosilane backbones
Sato, I
Kodaka, R
Hosoi, K
Soai, K
TETRAHEDRON-ASYMMETRY, 2002, 13 (08) : 805 - 808
[26] Development of Highly Active Chiral Titanium Catalysts for the Enantioselective Addition of Various Organometallic Reagents to Aldehydes
Harada, Toshiro
CHEMICAL RECORD, 2016, 16 (03): : 1256 - 1273
[27] Noscapine Derivatives as New Chiral Catalysts in Asymmetric Synthesis: Highly Enantioselective Addition of Diethylzinc to Aldehydes
Mohebbi, Maryam
Bararjanian, Morteza
Ebrahimi, Samad N.
Smiesko, Martin
Salehi, Peyman
SYNTHESIS-STUTTGART, 2018, 50 (09): : 1841 - 1848
[28] Highly enantioselective synthesis of chiral allylic alcohols by asymmetric addition of novel mixed reagents of trialkenylbismuthines/dialkylzincs to aldehydes
Sato, Itaru
Asakura, Noriaki
Iwashita, Taizo
TETRAHEDRON-ASYMMETRY, 2007, 18 (22) : 2638 - 2642
[29] HIGHLY ENANTIOSELECTIVE ALKYNYLATION OF ALDEHYDES PROMOTED BY CHIRAL OXAZABOROLIDINES
COREY, EJ
CIMPRICH, KA
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) : 3151 - 3152
[30] Highly enantioselective hydroamination to six-membered rings by heterobimetallic catalysts
Hussein, Lenard
Purkait, Nibadita
Biyikal, Mustafa
Tausch, Eugenia
Roesky, Peter W.
Blechert, Siegfried
CHEMICAL COMMUNICATIONS, 2014, 50 (29) : 3862 - 3864

← 1 2 3 4 5 →