Detailed Information on Publication Record
2010
Asymmetric Diels-Alder reaction using benzoin as a photoremovable chiral auxiliary
KAMMATH, Viju Balachandran, Peter ŠEBEJ, Tomáš SLANINA and Petr KLÁNBasic information
Original name
Asymmetric Diels-Alder reaction using benzoin as a photoremovable chiral auxiliary
Authors
KAMMATH, Viju Balachandran, Peter ŠEBEJ, Tomáš SLANINA and Petr KLÁN
Edition
240th American Chemical Society National Meeting & Exposition, 2010
Other information
Language
English
Type of outcome
Konferenční abstrakt
Field of Study
10401 Organic chemistry
Country of publisher
United States of America
Confidentiality degree
není předmětem státního či obchodního tajemství
References:
Organization unit
Faculty of Science
Keywords in English
Chiral Auxiliary, Photochemistry, Benzoin Moiety, Diels-Alder Reaction, Stereoselectivity
Změněno: 20/1/2011 23:17, Mgr. Peter Šebej, Ph.D.
V originále
Controlling the reaction stereochemistry is often achieved by using a chiral auxiliary which is covalently attached to the prochiral substrate before chirality relay is performed. These groups are optically active compounds or units that are temporarily incorporated to be utilized in the selective formation of one of the enantiomers. Here photoremovable chiral auxiliary (PCA) represents a new strategy in the field of asymmetric organic synthesis, which offers a chiral auxiliary that can be photochemically removed under specific conditions. The benzoin group is known to be a good photoremovable protecting group for a variety of functionalities, such as carboxylates, hydroxyls, phosphates etc. Since benzoin contains a chiral center, we proposed and studied its derivatives as PCA. Enantiopure benzoin group is connected to a dienophile which reacts with a diene in the presence of various catalysts. The auxiliary is then removed upon irradiation giving the products exhibiting enantiomeric excess.
In Czech
Controlling the reaction stereochemistry is often achieved by using a chiral auxiliary which is covalently attached to the prochiral substrate before chirality relay is performed. These groups are optically active compounds or units that are temporarily incorporated to be utilized in the selective formation of one of the enantiomers. Here photoremovable chiral auxiliary (PCA) represents a new strategy in the field of asymmetric organic synthesis, which offers a chiral auxiliary that can be photochemically removed under specific conditions. The benzoin group is known to be a good photoremovable protecting group for a variety of functionalities, such as carboxylates, hydroxyls, phosphates etc. Since benzoin contains a chiral center, we proposed and studied its derivatives as PCA. Enantiopure benzoin group is connected to a dienophile which reacts with a diene in the presence of various catalysts. The auxiliary is then removed upon irradiation giving the products exhibiting enantiomeric excess.
Links
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