| Nucleophilic catalysis with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) for the esterification of carboxylic acids with dimethyl carbonate. | |
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MedLine Citation:
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PMID: 11925227 Owner: NLM Status: PubMed-not-MEDLINE |
Abstract/OtherAbstract:
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1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) is an effective nucleophilic catalyst for carboxylic acid esterification with dimethyl carbonate (DMC). The reaction pathway of this new class of nucleophilic catalysis has been studied. A plausible, multistep mechanism is proposed, which involves an initial N-acylation of DBU with DMC to form a carbamate intermediate. Subsequent O-alkylation of the carboxylate with this intermediate generates the corresponding methyl ester in excellent yield. In the absence of DBU or in the presence of other bases, such as ammonium hydroxide or N-methylmorpholine, the same reaction affords no desired product. This method is particularly valuable for the synthesis of methyl esters that contain acid-sensitive functionality. |
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Authors:
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Wen-Chung Shieh; Steven Dell; Oljan Repic |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 67 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2002 Apr |
Date Detail:
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Created Date: 2002-04-01 Completed Date: 2002-07-17 Revised Date: 2003-11-03 |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 2188-91 Citation Subset: - |
Affiliation:
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Chemical and Analytical Development, Novartis Institute for Biomedical Research, East Hanover, New Jersey 07936, USA. wen.shieh@pharma.novartis.com |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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