Synthesis of β-Lactams from Diazoketones and Imines: The Use of Microwave Irradiation
The transformation of diazoketones derived from α-amino acids to ketenes that, in turn, react further with imines to afford β-lactams, can be realized not only by utilizing photochemical reaction conditions but also under the action of microwave irradiation. Under the latter reaction conditions 4-al...
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| Published in | Organic letters Vol. 3; no. 12; pp. 1849 - 1851 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
14.06.2001
Amer Chemical Soc |
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| Abstract | The transformation of diazoketones derived from α-amino acids to ketenes that, in turn, react further with imines to afford β-lactams, can be realized not only by utilizing photochemical reaction conditions but also under the action of microwave irradiation. Under the latter reaction conditions 4-alkenyl-substituted β-lactams derived from amino acids, substrates that were not previously accessible, have been prepared. β-Lactams possessing a trans-substitution pattern at the ring were obtained exclusively. |
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| AbstractList | [see reaction]. The transformation of diazoketones derived from alpha-amino acids to ketenes that, in turn, react further with imines to afford beta-lactams, can be realized not only by utilizing photochemical reaction conditions but also under the action of microwave irradiation. Under the latter reaction conditions 4-alkenyl-substituted beta-lactams derived from amino acids, substrates that were not previously accessible, have been prepared. beta-Lactams possessing a trans-substitution pattern at the ring were obtained exclusively. The transformation of diazoketones derived from α-amino acids to ketenes that, in turn, react further with imines to afford β-lactams, can be realized not only by utilizing photochemical reaction conditions but also under the action of microwave irradiation. Under the latter reaction conditions 4-alkenyl-substituted β-lactams derived from amino acids, substrates that were not previously accessible, have been prepared. β-Lactams possessing a trans-substitution pattern at the ring were obtained exclusively. [GRAPHICS] The transformation of diazoketones derived from alpha -amino acids to ketenes that, in turn, react further with imines to afford beta -lactams, can be realized not only by utilizing photochemical reaction conditions but also under the action of microwave irradiation. Under the latter reaction conditions 4-alkenyl substituted beta -lactams derived from amino acids, substrates that were not previously accessible, have been prepared. beta -actams possessing a trans-substitution pattern at the ring were obtained exclusively. |
| Author | Podlech, Joachim Linder, Michael R |
| Author_xml | – sequence: 1 givenname: Michael R surname: Linder fullname: Linder, Michael R – sequence: 2 givenname: Joachim surname: Podlech fullname: Podlech, Joachim |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/11405727$$D View this record in MEDLINE/PubMed |
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| Keywords | GV104326 ORGANIC-REACTION ENHANCEMENT ARNDT-EISTERT REACTION CHEMISTRY ALPHA-AMINO-ACIDS IN-VITRO ACTIVITY STEREOSELECTIVE SYNTHESIS |
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| Snippet | The transformation of diazoketones derived from α-amino acids to ketenes that, in turn, react further with imines to afford β-lactams, can be realized not only... [GRAPHICS] The transformation of diazoketones derived from alpha -amino acids to ketenes that, in turn, react further with imines to afford beta -lactams, can... [see reaction]. The transformation of diazoketones derived from alpha-amino acids to ketenes that, in turn, react further with imines to afford beta-lactams,... |
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| SubjectTerms | Azo Compounds - chemistry beta-Lactams - chemical synthesis beta-Lactams - chemistry Chemistry Chemistry, Organic Imines - chemistry Ketones - chemistry Microwaves Physical Sciences Science & Technology |
| Title | Synthesis of β-Lactams from Diazoketones and Imines: The Use of Microwave Irradiation |
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