Ruthenium‐Catalyzed Direct Asymmetric Reductive Amination of Diaryl and Sterically Hindered Ketones with Ammonium Salts and H2
A Ru‐catalyzed direct asymmetric reductive amination of ortho‐OH‐substituted diaryl and sterically hindered ketones with ammonium salts is reported. This method represents a straightforward route toward the synthesis of synthetically useful chiral primary diarylmethylamines and sterically hindered b...
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| Published in | Angewandte Chemie International Edition Vol. 59; no. 13; pp. 5321 - 5325 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
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23.03.2020
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| Edition | International ed. in English |
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| Abstract | A Ru‐catalyzed direct asymmetric reductive amination of ortho‐OH‐substituted diaryl and sterically hindered ketones with ammonium salts is reported. This method represents a straightforward route toward the synthesis of synthetically useful chiral primary diarylmethylamines and sterically hindered benzylamines (up to 97 % yield, 93–>99 % ee). Elaborations of the chiral amine products into bioactive compounds and a chiral ligand were demonstrated through manipulation of the removable and convertible ‐OH group.
OH yeah: A highly enantioselective OH‐assisted direct asymmetric reductive amination of diaryl and sterically hindered ketones with ammonium salts and H2 was developed. This reaction has a broad substrate scope (>30 examples) and offers straightforward access to synthetically useful chiral primary diarylmethylamines and sterically hindered benzylamines with high yield and enantioselectivity. |
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| AbstractList | A Ru-catalyzed direct asymmetric reductive amination of ortho-OH-substituted diaryl and sterically hindered ketones with ammonium salts is reported. This method represents a straightforward route toward the synthesis of synthetically useful chiral primary diarylmethylamines and sterically hindered benzylamines (up to 97 % yield, 93->99 % ee). Elaborations of the chiral amine products into bioactive compounds and a chiral ligand were demonstrated through manipulation of the removable and convertible -OH group.A Ru-catalyzed direct asymmetric reductive amination of ortho-OH-substituted diaryl and sterically hindered ketones with ammonium salts is reported. This method represents a straightforward route toward the synthesis of synthetically useful chiral primary diarylmethylamines and sterically hindered benzylamines (up to 97 % yield, 93->99 % ee). Elaborations of the chiral amine products into bioactive compounds and a chiral ligand were demonstrated through manipulation of the removable and convertible -OH group. A Ru‐catalyzed direct asymmetric reductive amination of ortho‐OH‐substituted diaryl and sterically hindered ketones with ammonium salts is reported. This method represents a straightforward route toward the synthesis of synthetically useful chiral primary diarylmethylamines and sterically hindered benzylamines (up to 97 % yield, 93–>99 % ee). Elaborations of the chiral amine products into bioactive compounds and a chiral ligand were demonstrated through manipulation of the removable and convertible ‐OH group. OH yeah: A highly enantioselective OH‐assisted direct asymmetric reductive amination of diaryl and sterically hindered ketones with ammonium salts and H2 was developed. This reaction has a broad substrate scope (>30 examples) and offers straightforward access to synthetically useful chiral primary diarylmethylamines and sterically hindered benzylamines with high yield and enantioselectivity. A Ru‐catalyzed direct asymmetric reductive amination of ortho‐OH‐substituted diaryl and sterically hindered ketones with ammonium salts is reported. This method represents a straightforward route toward the synthesis of synthetically useful chiral primary diarylmethylamines and sterically hindered benzylamines (up to 97 % yield, 93–>99 % ee). Elaborations of the chiral amine products into bioactive compounds and a chiral ligand were demonstrated through manipulation of the removable and convertible ‐OH group. |
| Author | Zhang, Yao Zhang, Qing‐Wen Zhang, Xumu Yin, Qin Hu, Le' an |
| Author_xml | – sequence: 1 givenname: Le' an surname: Hu fullname: Hu, Le' an organization: University of Macau – sequence: 2 givenname: Yao surname: Zhang fullname: Zhang, Yao organization: Southern University of Science and Technology – sequence: 3 givenname: Qing‐Wen surname: Zhang fullname: Zhang, Qing‐Wen organization: University of Macau – sequence: 4 givenname: Qin orcidid: 0000-0003-3534-3786 surname: Yin fullname: Yin, Qin email: yinq@sustech.edu.cn organization: Southern University of Science and Technology – sequence: 5 givenname: Xumu surname: Zhang fullname: Zhang, Xumu organization: Southern University of Science and Technology |
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| Snippet | A Ru‐catalyzed direct asymmetric reductive amination of ortho‐OH‐substituted diaryl and sterically hindered ketones with ammonium salts is reported. This... A Ru-catalyzed direct asymmetric reductive amination of ortho-OH-substituted diaryl and sterically hindered ketones with ammonium salts is reported. This... |
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| SubjectTerms | Amination amines Ammonium Ammonium salts Asymmetry Bioactive compounds diaryl ketones homogeneous catalysis Ketones reductive amination Ruthenium Salts |
| Title | Ruthenium‐Catalyzed Direct Asymmetric Reductive Amination of Diaryl and Sterically Hindered Ketones with Ammonium Salts and H2 |
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