(Dynamic) Kinetic Resolution of Enamines/Imines: Enantioselective N‐Heterocyclic Carbene Catalyzed [3+3] Annulation of Bromoenals and Enamines/Imines
The enantioselective N‐heterocyclic carbene catalyzed [3+3] annulation of α‐bromoenals by dynamic kinetic resolution (DKR) of enamines and normal resolution of α,α‐disubstituted imines were developed. The corresponding substituted dihydropyridones were isolated in good yields with excellent diastere...
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| Published in | Angewandte Chemie International Edition Vol. 58; no. 4; pp. 1183 - 1187 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
WEINHEIM
Wiley
21.01.2019
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| Edition | International ed. in English |
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| Abstract | The enantioselective N‐heterocyclic carbene catalyzed [3+3] annulation of α‐bromoenals by dynamic kinetic resolution (DKR) of enamines and normal resolution of α,α‐disubstituted imines were developed. The corresponding substituted dihydropyridones were isolated in good yields with excellent diastereo‐ and enantioselectivities, and a high selective factor (up to 83) was realized for the resolution of α,α‐disubstituted imines.
The S factor: The enantioselective N‐heterocyclic carbene (NHC) catalyzed [3+3] annulation of α‐bromoenals by dynamic kinetic resolution (DKR) of enamines, and normal resolution of α,α‐disubstituted imines were developed. The corresponding substituted dihydropyridones were isolated in good yields with excellent diastereo‐ and enantioselectivities, and a high selectivity factor was realized for the resolution of α,α‐disubstituted imines. |
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| AbstractList | The enantioselective N‐heterocyclic carbene catalyzed [3+3] annulation of α‐bromoenals by dynamic kinetic resolution (DKR) of enamines and normal resolution of α,α‐disubstituted imines were developed. The corresponding substituted dihydropyridones were isolated in good yields with excellent diastereo‐ and enantioselectivities, and a high selective factor (up to 83) was realized for the resolution of α,α‐disubstituted imines.
The S factor: The enantioselective N‐heterocyclic carbene (NHC) catalyzed [3+3] annulation of α‐bromoenals by dynamic kinetic resolution (DKR) of enamines, and normal resolution of α,α‐disubstituted imines were developed. The corresponding substituted dihydropyridones were isolated in good yields with excellent diastereo‐ and enantioselectivities, and a high selectivity factor was realized for the resolution of α,α‐disubstituted imines. The enantioselective N‐heterocyclic carbene catalyzed [3+3] annulation of α‐bromoenals by dynamic kinetic resolution (DKR) of enamines and normal resolution of α,α‐disubstituted imines were developed. The corresponding substituted dihydropyridones were isolated in good yields with excellent diastereo‐ and enantioselectivities, and a high selective factor (up to 83) was realized for the resolution of α,α‐disubstituted imines. The enantioselective N-heterocyclic carbene catalyzed [3+3] annulation of alpha-bromoenals by dynamic kinetic resolution (DKR) of enamines and normal resolution of alpha,alpha-disubstituted imines were developed. The corresponding substituted dihydropyridones were isolated in good yields with excellent diastereo- and enantioselectivities, and a high selective factor (up to 83) was realized for the resolution of alpha,alpha-disubstituted imines. |
| Author | Gao, Zhong‐Hua Ye, Song Chen, Kun‐Quan |
| Author_xml | – sequence: 1 givenname: Kun‐Quan surname: Chen fullname: Chen, Kun‐Quan organization: University of Chinese Academy of Sciences – sequence: 2 givenname: Zhong‐Hua surname: Gao fullname: Gao, Zhong‐Hua organization: Chinese Academy of Sciences – sequence: 3 givenname: Song orcidid: 0000-0002-3962-7738 surname: Ye fullname: Ye, Song email: songye@iccas.ac.cn organization: University of Chinese Academy of Sciences |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/30499624$$D View this record in MEDLINE/PubMed |
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| Keywords | N-heterocyclic carbene ASYMMETRIC TRANSFER HYDROGENATION ACTIVATION 2-BROMOENALS 1,3-DICARBONYL COMPOUNDS RECEPTOR ALKYNYL ALDEHYDES organocatalysis REARRANGEMENT annulations heterocycles DIHYDROPYRIDINONES ESTERS kinetic resolution STEREOSELECTIVE-SYNTHESIS |
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| SubjectTerms | annulations Chemical reactions Chemistry Chemistry, Multidisciplinary Enantiomers heterocycles Imines kinetic resolution N-heterocyclic carbene Organic chemistry organocatalysis Physical Sciences Science & Technology |
| Title | (Dynamic) Kinetic Resolution of Enamines/Imines: Enantioselective N‐Heterocyclic Carbene Catalyzed [3+3] Annulation of Bromoenals and Enamines/Imines |
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