Iridium-catalyzed diastereoselective amination of alcohols with chiral tert-butanesulfinamide by the use of a borrowing hydrogen methodology

被引：17

作者：

Xi, Xiaomei ^{[1
]}

Li, Yongjie ^{[1
]}

Wang, Guannan ^{[1
]}

Xu, Guangda ^{[1
]}

Shang, Lina ^{[1
]}

Zhang, Yao ^{[1
]}

Xia, Lixin ^{[1
]}

机构：

[1] Liaoning Univ, Coll Chem, Shenyang 110036, Liaoning, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2019年 / 17卷 / 33期

关键词：

ASYMMETRIC TRANSFER HYDROGENATION; N-ALKYLATION; COOPERATIVE CATALYSIS; REDUCTIVE AMINATION; SECONDARY ALCOHOLS; PRIMARY AMINES; IRIDACYCLE;

D O I：

10.1039/c9ob01417a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An iridium-catalyzed diastereoselective amination of alcohols with chiral tert-butanesulfinamide was developed under basic conditions, affording the optically active secondary sulfinamides in high yields and diastereoselectivities. The removal of the sulfinyl group from sulfonamides allowed a facile access to a wide range of alpha-chiral primary amines. This synthetic strategy was further applied in the synthesis of the marketed pharmaceuticals (S)-rivastigmine and NPS R-568.

引用

页码：7651 / 7654

页数：4

共 39 条

[1] Diastereoselective Iridium-Catalyzed Amination of Biosourced Isohexides Through Borrowing Hydrogen Methodology
Jacolot, Maiwenn
Moebs-Sanchez, Sylvie
Popowycz, Florence
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (16): : 9456 - 9463
[2] Diastereoselective iridium catalyzed amination of biosourced isohexides through borrowing hydrogen methodology
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Moebs, Sylvie
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ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
[3] Catalytic Enantioselective Amination of Alcohols by the Use of Borrowing Hydrogen Methodology: Cooperative Catalysis by Iridium and a Chiral Phosphoric Acid
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Lim, Ching-Si
Sim, Derek Sui Boon
Pan, Hui-Jie
Zhao, Yu
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (05) : 1399 - 1403
[4] Borrowing Hydrogen in Water and Ionic Liquids: Iridium-Catalyzed Alkylation of Amines with Alcohols
Saidi, Ourida
Blacker, A. John
Lamb, Gareth W.
Marsden, Stephen P.
Taylor, James E.
Williams, Jonathan M. J.
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[5] Ruthenium-Catalyzed Amination of Secondary Alcohols Using Borrowing Hydrogen Methodology
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Takacs, James M.
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[6] Selective Amine Cross-Coupling Using Iridium-Catalyzed "Borrowing Hydrogen" Methodology
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Blacker, A. John
Farah, Mohamed M.
Marsden, Stephen P.
Williams, Jonathan M. J.
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[7] Iridium-catalyzed, asymmetric amination of allylic alcohols activated by Lewis acids
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Gopalarathnam, Apsara
Hartwig, John F.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (24) : 7508 - +
[8] Direct, Enantioselective Iridium-Catalyzed Allylic Amination of Racemic Allylic Alcohols
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Roggen, Markus
Carreira, Erick M.
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[9] A Vinyl Cyclopropane Ring Expansion and Iridium-Catalyzed Hydrogen Borrowing Cascade
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Cheong, Choon Boon
Frost, James R.
Christensen, Kirsten E.
Donohoe, Timothy J.
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[10] A Vinyl Cyclopropane Ring Expansion and Iridium-Catalyzed Hydrogen Borrowing Cascade
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Cheong, Choon Boon
Frost, James R.
Christensen, Kirsten E.
Donohoe, Timothy J.
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