Carbonyl catalysis enables a biomimetic asymmetric Mannich reaction
Chen, J., Gong, X., Li, J., Li, Y., Ma, J., Hou, C., Zhao, G., Yuan, W., Zhao, B.
American Association for the Advancement of Science (AAAS)
Published 2018
American Association for the Advancement of Science (AAAS)
Published 2018
| Publication Date: |
2018-06-29
|
|---|---|
| Publisher: |
American Association for the Advancement of Science (AAAS)
|
| Print ISSN: |
0036-8075
|
| Electronic ISSN: |
1095-9203
|
| Topics: |
Biology
Chemistry and Pharmacology
Geosciences
Computer Science
Medicine
Natural Sciences in General
Physics
|
| Keywords: |
Chemistry
|
| Published by: |
| _version_ | 1836398990814347264 |
|---|---|
| autor | Chen, J., Gong, X., Li, J., Li, Y., Ma, J., Hou, C., Zhao, G., Yuan, W., Zhao, B. |
| beschreibung | Chiral amines are widely used as catalysts in asymmetric synthesis to activate carbonyl groups for α-functionalization. Carbonyl catalysis reverses that strategy by using a carbonyl group to activate a primary amine. Inspired by biological carbonyl catalysis, which is exemplified by reactions of pyridoxal-dependent enzymes, we developed an N-quaternized pyridoxal catalyst for the asymmetric Mannich reaction of glycinate with aryl N -diphenylphosphinyl imines. The catalyst exhibits high activity and stereoselectivity, likely enabled by enzyme-like cooperative bifunctional activation of the substrates. Our work demonstrates the catalytic utility of the pyridoxal moiety in asymmetric catalysis. |
| citation_standardnr | 6295172 |
| datenlieferant | ipn_articles |
| feed_id | 25 |
| feed_publisher | American Association for the Advancement of Science (AAAS) |
| feed_publisher_url | http://www.aaas.org/ |
| insertion_date | 2018-06-29 |
| journaleissn | 1095-9203 |
| journalissn | 0036-8075 |
| publikationsjahr_anzeige | 2018 |
| publikationsjahr_facette | 2018 |
| publikationsjahr_intervall | 7984:2015-2019 |
| publikationsjahr_sort | 2018 |
| publisher | American Association for the Advancement of Science (AAAS) |
| quelle | Science |
| relation | http://science.sciencemag.org/cgi/content/short/360/6396/1438?rss=1 |
| schlagwort | Chemistry |
| search_space | articles |
| shingle_author_1 | Chen, J., Gong, X., Li, J., Li, Y., Ma, J., Hou, C., Zhao, G., Yuan, W., Zhao, B. |
| shingle_author_2 | Chen, J., Gong, X., Li, J., Li, Y., Ma, J., Hou, C., Zhao, G., Yuan, W., Zhao, B. |
| shingle_author_3 | Chen, J., Gong, X., Li, J., Li, Y., Ma, J., Hou, C., Zhao, G., Yuan, W., Zhao, B. |
| shingle_author_4 | Chen, J., Gong, X., Li, J., Li, Y., Ma, J., Hou, C., Zhao, G., Yuan, W., Zhao, B. |
| shingle_catch_all_1 | Carbonyl catalysis enables a biomimetic asymmetric Mannich reaction Chemistry Chiral amines are widely used as catalysts in asymmetric synthesis to activate carbonyl groups for α-functionalization. Carbonyl catalysis reverses that strategy by using a carbonyl group to activate a primary amine. Inspired by biological carbonyl catalysis, which is exemplified by reactions of pyridoxal-dependent enzymes, we developed an N-quaternized pyridoxal catalyst for the asymmetric Mannich reaction of glycinate with aryl N -diphenylphosphinyl imines. The catalyst exhibits high activity and stereoselectivity, likely enabled by enzyme-like cooperative bifunctional activation of the substrates. Our work demonstrates the catalytic utility of the pyridoxal moiety in asymmetric catalysis. Chen, J., Gong, X., Li, J., Li, Y., Ma, J., Hou, C., Zhao, G., Yuan, W., Zhao, B. American Association for the Advancement of Science (AAAS) 0036-8075 00368075 1095-9203 10959203 |
| shingle_catch_all_2 | Carbonyl catalysis enables a biomimetic asymmetric Mannich reaction Chemistry Chiral amines are widely used as catalysts in asymmetric synthesis to activate carbonyl groups for α-functionalization. Carbonyl catalysis reverses that strategy by using a carbonyl group to activate a primary amine. Inspired by biological carbonyl catalysis, which is exemplified by reactions of pyridoxal-dependent enzymes, we developed an N-quaternized pyridoxal catalyst for the asymmetric Mannich reaction of glycinate with aryl N -diphenylphosphinyl imines. The catalyst exhibits high activity and stereoselectivity, likely enabled by enzyme-like cooperative bifunctional activation of the substrates. Our work demonstrates the catalytic utility of the pyridoxal moiety in asymmetric catalysis. Chen, J., Gong, X., Li, J., Li, Y., Ma, J., Hou, C., Zhao, G., Yuan, W., Zhao, B. American Association for the Advancement of Science (AAAS) 0036-8075 00368075 1095-9203 10959203 |
| shingle_catch_all_3 | Carbonyl catalysis enables a biomimetic asymmetric Mannich reaction Chemistry Chiral amines are widely used as catalysts in asymmetric synthesis to activate carbonyl groups for α-functionalization. Carbonyl catalysis reverses that strategy by using a carbonyl group to activate a primary amine. Inspired by biological carbonyl catalysis, which is exemplified by reactions of pyridoxal-dependent enzymes, we developed an N-quaternized pyridoxal catalyst for the asymmetric Mannich reaction of glycinate with aryl N -diphenylphosphinyl imines. The catalyst exhibits high activity and stereoselectivity, likely enabled by enzyme-like cooperative bifunctional activation of the substrates. Our work demonstrates the catalytic utility of the pyridoxal moiety in asymmetric catalysis. Chen, J., Gong, X., Li, J., Li, Y., Ma, J., Hou, C., Zhao, G., Yuan, W., Zhao, B. American Association for the Advancement of Science (AAAS) 0036-8075 00368075 1095-9203 10959203 |
| shingle_catch_all_4 | Carbonyl catalysis enables a biomimetic asymmetric Mannich reaction Chemistry Chiral amines are widely used as catalysts in asymmetric synthesis to activate carbonyl groups for α-functionalization. Carbonyl catalysis reverses that strategy by using a carbonyl group to activate a primary amine. Inspired by biological carbonyl catalysis, which is exemplified by reactions of pyridoxal-dependent enzymes, we developed an N-quaternized pyridoxal catalyst for the asymmetric Mannich reaction of glycinate with aryl N -diphenylphosphinyl imines. The catalyst exhibits high activity and stereoselectivity, likely enabled by enzyme-like cooperative bifunctional activation of the substrates. Our work demonstrates the catalytic utility of the pyridoxal moiety in asymmetric catalysis. Chen, J., Gong, X., Li, J., Li, Y., Ma, J., Hou, C., Zhao, G., Yuan, W., Zhao, B. American Association for the Advancement of Science (AAAS) 0036-8075 00368075 1095-9203 10959203 |
| shingle_title_1 | Carbonyl catalysis enables a biomimetic asymmetric Mannich reaction |
| shingle_title_2 | Carbonyl catalysis enables a biomimetic asymmetric Mannich reaction |
| shingle_title_3 | Carbonyl catalysis enables a biomimetic asymmetric Mannich reaction |
| shingle_title_4 | Carbonyl catalysis enables a biomimetic asymmetric Mannich reaction |
| timestamp | 2025-06-30T23:35:51.966Z |
| titel | Carbonyl catalysis enables a biomimetic asymmetric Mannich reaction |
| titel_suche | Carbonyl catalysis enables a biomimetic asymmetric Mannich reaction |
| topic | W V TE-TZ SQ-SU WW-YZ TA-TD U |
| uid | ipn_articles_6295172 |