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Enantiopure Quaternary α-Trifluoromethyl-α-alkoxyaldehydes from L-Tartaric Acid Derived Ketoamides.
- Source :
-
Journal of Organic Chemistry . 10/17/2008, Vol. 73 Issue 20, p7990-7995. 6p. 4 Diagrams, 5 Charts. - Publication Year :
- 2008
-
Abstract
- The diastereoselective nucleophilic trifluoromethylation of a range of ketoamides derived from L-tartaric acid has been studied. TMSCF3 in the presence of a catalytic amount of K2CO3 in DMF has been identified as the conditions leading to the highest diastereoselectivities. A sequential one-pot reaction trifluoromethylation-etherification of the trifluoromethylcarbinol has been developed. Only one further one-pot reaction, ketal hydrolysis-oxidative cleavage, led to the final α-trifluoromethylated α-alkoxy-aldehydes. This procedure was applied to the preparation of a series of enantiopure aryl, heteroaryl, and alkyl α-trifluoromethyl-α-alkoxyaldehydes [ABSTRACT FROM AUTHOR]
- Subjects :
- *ALDEHYDES
*TARTARIC acid
*AMIDES
*METHYLATION
*NUCLEOPHILIC reactions
Subjects
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 73
- Issue :
- 20
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 35024560
- Full Text :
- https://doi.org/10.1021/jo8013403