Gold-catalyzed intermolecular hydroamination of allenes with arylamines and resulting high chirality transfer

被引：220

作者：

Nishina, Naoko ^{[1
]}

Yamamoto, Yoshinori ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 20期

关键词：

allenes; allylic compounds; gold; hydroamination;

D O I：

10.1002/anie.200600331

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Au contraire! Contrary to the relatively well-studied metal-catalyzed intramolecular hydroamination of allenes, the intermolecular reaction is rare and is here accomplished with a gold (III) catalyst. Aryl amines 2 react with chiral allenes 1 in the presence of AuBr 3 at ambient temperature to produce chiral allylamines 3 (Ar = Ph; o-, m-, p-CH3C6H4) in good yields with high ee values. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：3314 / 3317

页数：4

共 59 条

[1] Use of group 4 bis(sulfonamido) complexes in the intramolecular hydroamination of alkynes and allenes [J].

Ackermann, L ;

Bergman, RG ;

Loy, RN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (39) :11956-11963

[2] A highly reactive titanium precatalyst for intramolecular hydroamination reactions [J].

Ackermann, L ;

Bergman, RG .

ORGANIC LETTERS, 2002, 4 (09) :1475-1478

[3] Palladium-catalyzed hydrocarboxylation of allenes [J].

Al-Masum, M ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (15) :3809-3810

[4] The two component palladium catalyst system for intermolecular hydroamination of allenes [J].

AlMasum, M ;

Meguro, M ;

Yamamoto, Y .

TETRAHEDRON LETTERS, 1997, 38 (34) :6071-6074

[5]

Amombo MO, 1999, SYNLETT, P1871

[6]

[Anonymous], 2005, ANGEW CHEM, V117, P7150, DOI DOI 10.1002/ANGE.200502735

[7]

Arcadi A, 2001, ADV SYNTH CATAL, V343, P443, DOI 10.1002/1615-4169(200107)343:5<443::AID-ADSC443>3.3.CO

[8]

2-R

[9] Intramolecular hydroamination cyclization of aminoallenes catalyzed by organolanthanide complexes. Scope and mechanistic aspects [J].

Arredondo, VM ;

McDonald, FE ;

Marks, TJ .

ORGANOMETALLICS, 1999, 18 (10) :1949-1960

[10] Organolanthanide-catalyzed hydroamination/cyclization. Efficient allene-based transformations for the syntheses of naturally occurring alkaloids [J].

Arredondo, VM ;

Tian, S ;

McDonald, FE ;

Marks, TJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (15) :3633-3639

← 1 2 3 4 5 6 →