Asymmetric Palladium-Catalyzed Carboamination Reactions for the Synthesis of Enantiomerically Enriched 2-(Arylmethyl)- and 2-(Alkenylmethyl)pyrrolidines

被引：170

作者：

Mai, Duy N. ^{[1
]}

Wolfe, John P. ^{[1
]}

机构：

[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 35期

关键词：

STEREOSELECTIVE-SYNTHESIS; CONJUGATED DIENES; MONODENTATE PHOSPHORAMIDITES; CIS-AMINOPALLADATION; ALKENES; PYRROLIDINES; DIAMINATION; ARYL; HETEROCYCLES; CARBOETHERIFICATION;

D O I：

10.1021/ja106989h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The enantioselective synthesis of 2-(arylmethyl)- and 2-(alkenylmethyl)pyrrolidine derivatives via Pd-catalyzed alkene carboamination reactions is described. These transformations generate enantiomerically enriched products with up to 94% ee from readily available alkenyl or aryl bromides and N-boc-pent-4-enylamines. The application of this method to a concise asymmetric synthesis of (-)-tylophorine is also discussed.

引用

收藏

页码：12157 / 12159

页数：3

相关论文

共 38 条

[1] Diastereoselective Synthesis of Hexahydro-3H-pyrrolyzin-3-ones through Pd-Catalyzed Carboamination [J].

Bagnoli, Luana ;

Cacchi, Sandro ;

Fabrizi, Giancarlo ;

Goggiamani, Antonella ;

Scarponi, Catalina ;

Tiecco, Marcello .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (06) :2134-2137

[2] Solvent-Enhanced Diastereo- and Regioselectivity in the PdII-Catalyzed Synthesis of Six- and Eight-Membered Heterocycles via cis-Aminopalladation [J].

Balazs, Arpad ;

Hetenyi, Anasztazia ;

Szakonyi, Zsolt ;

Sillanpaa, Reijo ;

Fulop, Ferenc .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (30) :7376-7381

[3] Stereoselective synthesis of N-protected pyrrolidines via Pd-catalyzed reactions of γ-(N-acylamino) alkenes and γ-(N-Boc-amino) alkenes with aryl bromides [J].

Bertrand, MB ;

Wolfe, JP .

TETRAHEDRON, 2005, 61 (26) :6447-6459

[4] Mild Conditions for Pd-Catalyzed Carboamination of N-Protected Hex-4-enylamines and 1-, 3-, and 4-Substituted Pent-4-enylamines. Scope, Limitations, and Mechanism of Pyrrolidine Formation [J].

Bertrand, Myra Beaudoin ;

Neukom, Joshua D. ;

Wolfe, John P. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (22) :8851-8860

[5] A concise stereoselective synthesis of Preussin, 3-epi-Preussin, and analogues [J].

Bertrand, Myra Beaudoin ;

Wolfe, John P. .

ORGANIC LETTERS, 2006, 8 (11) :2353-2356

[6] Discovery of 5-arylsulfonamido-3(pyrrolidin-2-ylmethyl)-1H-indole derivatives as potent, selective 5-HT6 receptor agonists and antagonists [J].

Cole, DC ;

Lennox, WJ ;

Lombardi, S ;

Ellingboe, JW ;

Bernotas, RC ;

Tawa, GJ ;

Mazandarani, H ;

Smith, DL ;

Zhang, GM ;

Coupet, J ;

Schechter, LE .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (02) :353-356

[7] The asymmetric intramolecular Heck reaction in natural product total synthesis [J].

Dounay, AB ;

Overman, LE .

CHEMICAL REVIEWS, 2003, 103 (08) :2945-2963

[8] Catalytic asymmetric diamination of conjugated dienes and triene [J].

Du, Haifeng ;

Yuan, Weicheng ;

Zhao, Baoguo ;

Shi, Yian .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (38) :11688-+

[9] A facile Pd(0)-catalyzed regio- and stereoselective diamination of conjugated dienes and trienes [J].

Du, Haifeng ;

Zhao, Baoguo ;

Shi, Yian .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (04) :762-763

[10] Total syntheses of the tylophora alkaloids cryptopleurine, (-)-antofine, (-)-tylophorine, and (-)-ficuseptine C [J].

Fuerstner, Alois ;

Kennedy, Jason W. J. .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (28) :7398-7410

← 1 2 3 4 →