Asymmetric Diels-Alder reaction using benzoin as a photoremovable chiral auxiliary

KAMMATH, Viju Balachandran, Peter ŠEBEJ, Tomáš SLANINA a Petr KLÁN. Asymmetric Diels-Alder reaction using benzoin as a photoremovable chiral auxiliary. In 240th American Chemical Society National Meeting & Exposition. 2010.

Základní 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

• Originální jazyk: angličtina
• Typ výsledku: Konferenční abstrakt
• Obor: 10401 Organic chemistry
• Stát vydavatele: Spojené státy
• Utajení: není předmětem státního či obchodního tajemství
• WWW: 240th National ACS Meeting
• Organizační jednotka: Přírodovědecká fakulta
• Klíčová slova anglicky: Chiral Auxiliary, Photochemistry, Benzoin Moiety, Diels-Alder Reaction, Stereoselectivity
• Štítky: Benzoin Moiety, chiral auxiliary, Diels-Alder Reaction, Photochemistry, stereoselectivity

Anotace

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.

Anotace 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

• ME09021, projekt VaV: Název: Vývoj nových fotoaktivovatelných systémů pro biologické studie

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Vývoj nových fotoaktivovatelných systémů pro biologické studie, Program výzkumu a vývoje KONTAKT (ME)