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@proceedings{921802, author = {Kammath, Viju Balachandran and Šebej, Peter and Slanina, Tomáš and Klán, Petr}, booktitle = {240th American Chemical Society National Meeting & Exposition}, keywords = {Chiral Auxiliary, Photochemistry, Benzoin Moiety, Diels-Alder Reaction, Stereoselectivity}, language = {eng}, title = {Asymmetric Diels-Alder reaction using benzoin as a photoremovable chiral auxiliary}, url = {http://portal.acs.org/portal/acs/corg/content?_nfpb=true&_pageLabel=PP_SUPERARTICLE&node_id=2061&use_sec=false&sec_url_var=region1&__uuid=0de95170-e7c7-4285-9a31-52902a9c6c80}, year = {2010} }
TY - CONF ID - 921802 AU - Kammath, Viju Balachandran - Šebej, Peter - Slanina, Tomáš - Klán, Petr PY - 2010 TI - Asymmetric Diels-Alder reaction using benzoin as a photoremovable chiral auxiliary KW - Chiral Auxiliary, Photochemistry, Benzoin Moiety, Diels-Alder Reaction, Stereoselectivity UR - http://portal.acs.org/portal/acs/corg/content?_nfpb=true&_pageLabel=PP_SUPERARTICLE&node_id=2061&use_sec=false&sec_url_var=region1&__uuid=0de95170-e7c7-4285-9a31-52902a9c6c80 N2 - 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. ER -
KAMMATH, Viju Balachandran, Peter ŠEBEJ, Tomáš SLANINA a Petr KLÁN. Asymmetric Diels-Alder reaction using benzoin as a photoremovable chiral auxiliary. In \textit{240th American Chemical Society National Meeting \&{} Exposition}. 2010.
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