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.

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页码：564 / 567

页数：4

相关论文

共 61 条

[41] Pyrrole, pyrrolidine, pyridine, piperidine and tropane alkaloids [J].

O'Hagan, D .

NATURAL PRODUCT REPORTS, 2000, 17 (05) :435-446

[42] Catalytic asymmetric intramolecular hydroamination of aminoalkenes [J].

Ogata, Tokutaro ;

Ujihara, Atsushi ;

Tsuchida, Susumu ;

Shimizu, Tomoko ;

Kaneshige, Atsunori ;

Tomioka, Kiyoshi .

TETRAHEDRON LETTERS, 2007, 48 (38) :6648-6650

[43] A highly active catalyst for palladium-catalyzed cross-coupling reactions: Room-temperature Suzuki couplings and amination of unactivated aryl chlorides [J].

Old, DW ;

Wolfe, JP ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (37) :9722-9723

[44] Palladium-catalyzed intramolecular asymmetric hydroamination, hydroalkoxylation, and hydrocarbonation of alkynes [J].

Patil, Nitin T. ;

Lutete, Leopold Mpaka ;

Wu, Huanyou ;

Pahadi, Nirmal K. ;

Gridnev, Ilya D. ;

Yamamoto, Yoshinori .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (11) :4270-4279

[45] RAPID DEBENZYLATION OF N-BENZYLAMINO DERIVATIVES TO AMINO-DERIVATIVES USING AMMONIUM FORMATE AS CATALYTIC HYDROGEN TRANSFER AGENT [J].

RAM, S ;

SPICER, LD .

TETRAHEDRON LETTERS, 1987, 28 (05) :515-516

[46] Enantioselective intramolecular hydroamination catalyzed by lanthanide ate complexes coordinated by N-substituted (R)-1,1′-binaphthyl-2,2′-diamido ligands [J].

Riegert, D ;

Collin, J ;

Meddour, A ;

Schulz, E ;

Trifonov, A .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (06) :2514-2517

[47] Enantioselective catalytic hydroamination of alkenes [J].

Roesky, PW ;

Müller, TE .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (24) :2708-2710

[48] Biaryl phosphane ligands in palladium-catalyzed amination [J].

Surry, David S. ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (34) :6338-6361

[49] Rhodium-catalyzed intramolecular, anti-Markovnikov hydroamination. Synthesis of 3-arylpiperidines [J].

Takemiya, Akihiro ;

Hartwig, John F. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (18) :6042-6043

[50] Rhodium-catalyzed anti-Markovnikov hydroamination of vinylarenes [J].

Utsunomiya, M ;

Kuwano, R ;

Kawatsura, M ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (19) :5608-5609

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