Rhodium-Catalyzed Asymmetric Intramolecular Hydroamination of Unactivated Alkenes

被引：144

作者：

Shen, Xiaoqiang ^{[1
]}

Buchwald, Stephen L. ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 03期

基金：

美国国家卫生研究院;

关键词：

asymmetric catalysis; heterocycles; hydroamination; P ligands; rhodium; ANTI-MARKOVNIKOV HYDROAMINATION; HIGHLY-ACTIVE CATALYST; INTERMOLECULAR HYDROAMINATION; AMIDATE COMPLEXES; LIGANDS; VINYLARENES; AMINATION; NITROGEN; ALLENES; CARBON;

D O I：

10.1002/anie.200905402

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Figure Presented) One for the Rh(oad): The first rhodiumcatalyzed asymmetric intramolecular hydroamination of unactivated olefins was developed by using dialkylbiaryl phosphine ligands (see scheme; cod = 1,5-cyclooctadiene, Cy = cyclohexyl). A variety of 2-methylpyrrolidines have been synthesized with high enantioselectivities. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

收藏

页码：564 / 567

页数：4

相关论文

共 61 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], 2009, ASYMMETRIC SYNTHESIS

[4] Novel electron-rich bulky phosphine ligands facilitate the palladium-catalyzed preparation of diaryl ethers [J].

Aranyos, A ;

Old, DW ;

Kiyomori, A ;

Wolfe, JP ;

Sadighi, JP ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (18) :4369-4378

[5] Kinetic resolutions of indolines by a nonenzymatic acylation catalyst [J].

Arp, Forrest O. ;

Fu, Gregory C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (44) :14264-14265

[6] Platinum-catalyzed intramolecular hydroamination of unactivated olefins with secondary alkylamines [J].

Bender, CF ;

Widenhoefer, RA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (04) :1070-1071

[7] Sterically hindered mono(phosphines) as supporting ligands for the platinum-catalyzed hydroamination of amino alkenes [J].

Bender, Christopher F. ;

Hudson, William B. ;

Widenhoefer, Ross A. .

ORGANOMETALLICS, 2008, 27 (10) :2356-2358

[8] The enantioselective intramolecular aminative functionalization of unactivated alkenes, dienes, allenes and alkynes for the synthesis of chiral nitrogen heterocycles [J].

Chemler, Sherry R. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (15) :3009-3019

[9] Catalytic asymmetric vinylation of ketone enolates [J].

Chieffi, A ;

Kamikawa, K ;

Åhman, J ;

Fox, JM ;

Buchwald, SL .

ORGANIC LETTERS, 2001, 3 (12) :1897-1900

[10] Lanthanide complexes coordinated by N-substituted (R)-1,1′-binaphthyl-2,2′-diamido ligands in the catalysis of enantioselective intramolecular hydroamination [J].

Collin, J ;

Daran, JC ;

Jacquet, O ;

Schulz, E ;

Trifonov, A .

CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (11) :3455-3462

← 1 2 3 4 5 6 7 →