The Amino Thiourea-Catalyzed Asymmetric Nucleophilic Reactions
Bifunctional amino thiourea-catalyzed asymmetric additions of several nucleophiles into electron-deficient unsaturated compounds such as nitroolefins, ?,?-unsaturated imides, imines, and azodicarboxylates are described. We discovered that bifunctional thioureas bearing a tertiary amino gro...
| Main Authors: | , |
|---|---|
| Format: | Article |
| Language: | deu |
| Published: |
Swiss Chemical Society
2007-05-01
|
| Series: | CHIMIA |
| Subjects: | |
| Online Access: | https://chimia.ch/chimia/article/view/4323 |
| _version_ | 1811320339625410560 |
|---|---|
| author | Yoshiji Takemoto Hideto Miyabe |
| author_facet | Yoshiji Takemoto Hideto Miyabe |
| author_sort | Yoshiji Takemoto |
| collection | DOAJ |
| description |
Bifunctional amino thiourea-catalyzed asymmetric additions of several nucleophiles into electron-deficient unsaturated compounds such as nitroolefins, ?,?-unsaturated imides, imines, and azodicarboxylates are described. We discovered that bifunctional thioureas bearing a
tertiary amino group significantly accelerated several nucleophilic addition reactions of active methylene compounds to electron-deficient double bonds. In these reactions, a strong hydrogen-bonding ability of the thiourea moiety as well as an appropriate Brønsted basicity of the tertiary
amine is crucial for high enantioselectivity. This dual activation of both nucleophiles and electrophiles by the bifunctional thiourea expanded the applicability of the thiourea-catalyzed enantioselective reaction. In addition, these organocatalyzed asymmetric reactions were successfully applied
to the concise asymmetric synthesis of natural products and medicinal candidates such as epibatidine, baclofen, and CP-99,994.
|
| first_indexed | 2024-04-13T12:57:46Z |
| format | Article |
| id | doaj.art-9b0eb72c4b444978ae1e98c9ed3fddbb |
| institution | Directory Open Access Journal |
| issn | 0009-4293 2673-2424 |
| language | deu |
| last_indexed | 2024-04-13T12:57:46Z |
| publishDate | 2007-05-01 |
| publisher | Swiss Chemical Society |
| record_format | Article |
| series | CHIMIA |
| spelling | doaj.art-9b0eb72c4b444978ae1e98c9ed3fddbb2022-12-22T02:46:00ZdeuSwiss Chemical SocietyCHIMIA0009-42932673-24242007-05-0161510.2533/chimia.2007.269The Amino Thiourea-Catalyzed Asymmetric Nucleophilic ReactionsYoshiji TakemotoHideto Miyabe Bifunctional amino thiourea-catalyzed asymmetric additions of several nucleophiles into electron-deficient unsaturated compounds such as nitroolefins, ?,?-unsaturated imides, imines, and azodicarboxylates are described. We discovered that bifunctional thioureas bearing a tertiary amino group significantly accelerated several nucleophilic addition reactions of active methylene compounds to electron-deficient double bonds. In these reactions, a strong hydrogen-bonding ability of the thiourea moiety as well as an appropriate Brønsted basicity of the tertiary amine is crucial for high enantioselectivity. This dual activation of both nucleophiles and electrophiles by the bifunctional thiourea expanded the applicability of the thiourea-catalyzed enantioselective reaction. In addition, these organocatalyzed asymmetric reactions were successfully applied to the concise asymmetric synthesis of natural products and medicinal candidates such as epibatidine, baclofen, and CP-99,994. https://chimia.ch/chimia/article/view/4323AsymmetryCatalysisImineMalonateNitroolefinThiourea |
| spellingShingle | Yoshiji Takemoto Hideto Miyabe The Amino Thiourea-Catalyzed Asymmetric Nucleophilic Reactions CHIMIA Asymmetry Catalysis Imine Malonate Nitroolefin Thiourea |
| title | The Amino Thiourea-Catalyzed Asymmetric Nucleophilic Reactions |
| title_full | The Amino Thiourea-Catalyzed Asymmetric Nucleophilic Reactions |
| title_fullStr | The Amino Thiourea-Catalyzed Asymmetric Nucleophilic Reactions |
| title_full_unstemmed | The Amino Thiourea-Catalyzed Asymmetric Nucleophilic Reactions |
| title_short | The Amino Thiourea-Catalyzed Asymmetric Nucleophilic Reactions |
| title_sort | amino thiourea catalyzed asymmetric nucleophilic reactions |
| topic | Asymmetry Catalysis Imine Malonate Nitroolefin Thiourea |
| url | https://chimia.ch/chimia/article/view/4323 |
| work_keys_str_mv | AT yoshijitakemoto theaminothioureacatalyzedasymmetricnucleophilicreactions AT hidetomiyabe theaminothioureacatalyzedasymmetricnucleophilicreactions AT yoshijitakemoto aminothioureacatalyzedasymmetricnucleophilicreactions AT hidetomiyabe aminothioureacatalyzedasymmetricnucleophilicreactions |