2010
Asymmetric Diels-Alder reaction using benzoin as a photoremovable chiral auxiliary
KAMMATH, Viju Balachandran; Peter ŠEBEJ; Tomáš SLANINA a Petr KLÁNZákladní údaje
Originální název
Asymmetric Diels-Alder reaction using benzoin as a photoremovable chiral auxiliary
Autoři
KAMMATH, Viju Balachandran; Peter ŠEBEJ; Tomáš SLANINA a Petr KLÁN
Vydání
240th American Chemical Society National Meeting & Exposition, 2010
Další údaje
Jazyk
angličtina
Typ výsledku
Konferenční abstrakt
Obor
10401 Organic chemistry
Stát vydavatele
Spojené státy
Utajení
není předmětem státního či obchodního tajemství
Odkazy
Označené pro přenos do RIV
Ne
Organizační jednotka
Přírodovědecká fakulta
Klíčová slova anglicky
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.
Česky
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.
Návaznosti
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