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

被引：62

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 82 条

[1] Asymmetric hydroamination of non-activated carbon-carbon multiple bonds [J].

Aillaud, Isabelle ;

Collin, Jacqueline ;

Hannedouche, Jerome ;

Schulz, Emmanuelle .

DALTON TRANSACTIONS, 2007, (44) :5105-5118

[2]

[Anonymous], 2003, ANGEW CHEM-GER EDIT

[3]

[Anonymous], 2010, Angew. Chem.

[4]

[Anonymous], 2000, Templated organic synthesis

[5]

[Anonymous], 2003, ANGEW CHEM

[6] STEREOCONTROLLED RADICAL REACTIONS IN CARBOHYDRATE AND NUCLEOSIDE CHEMISTRY [J].

BARTON, DHR ;

GERO, SD ;

QUICLETSIRE, B ;

SAMADI, M .

TETRAHEDRON-ASYMMETRY, 1994, 5 (11) :2123-2136

[7]

Beauchemin A. M., 2008, ANGEW CHEM, V120, P1432

[8] Intermolecular cope-type hydroamination of alkenes and alkynes [J].

Beauchemin, Andre M. ;

Moran, Joseph ;

Lebrun, Marie-Eve ;

Seguin, Catherine ;

Dimitrijevic, Elena ;

Zhang, Lili ;

Gorelsky, Serge I. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (08) :1410-1413

[9] The catalytic intermolecular orthoarylation of phenols [J].

Bedford, RB ;

Coles, SJ ;

Hursthouse, MB ;

Limmert, ME .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (01) :112-114

[10] Factors influencing the reverse-Cope approach to 1,2,5-oxadiazinanes from allylamines and nitrones: Optimization of a new vicinal diamine synthesis [J].

Bell, KE ;

Coogan, MP ;

Gravestock, MB ;

Knight, DW ;

Thornton, SR .

TETRAHEDRON LETTERS, 1997, 38 (49) :8545-8548

← 1 2 3 4 5 6 7 8 9 →