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A highly stereoselective synthesis of glycidic amides based on a new class of chiral sulfonium salts: applications in asymmetric synthesis.
- Source :
-
Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2012 Nov 19; Vol. 18 (47), pp. 15190-201. Date of Electronic Publication: 2012 Oct 18. - Publication Year :
- 2012
-
Abstract
- A new type of chiral sulfonium salts that are characterized by a bicyclic system has been designed and synthesized from α-amino acids. Their corresponding ylides, which were prepared by basic treatment of the sulfonium salts, reacted smoothly with a broad array of simple and chiral aldehydes to provide trans-epoxy amides in reasonable to very good yields and excellent stereoselectivities (>98%). The obtained epoxy amides were found to be useful as synthetic building blocks. Thus, they were reduced into their corresponding epoxy alcohols and subjected to oxirane-ring-opening reactions with different types of nucleophiles.<br /> (Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)
- Subjects :
- Amides chemistry
Amino Acids chemistry
Epoxy Compounds chemistry
Molecular Structure
Propionates chemistry
Salts chemistry
Stereoisomerism
Sulfonium Compounds chemistry
Amides chemical synthesis
Epoxy Compounds chemical synthesis
Propionates chemical synthesis
Sulfonium Compounds chemical synthesis
Subjects
Details
- Language :
- English
- ISSN :
- 1521-3765
- Volume :
- 18
- Issue :
- 47
- Database :
- MEDLINE
- Journal :
- Chemistry (Weinheim an der Bergstrasse, Germany)
- Publication Type :
- Academic Journal
- Accession number :
- 23081826
- Full Text :
- https://doi.org/10.1002/chem.201201332