Enantioselective Synthesis of Bicyclopentane-Containing Alcohols via Asymmetric Transfer Hydrogenation
نویسندگان
چکیده
Compounds a containing bicyclo[1.1.1]pentane (BCP) adjacent to chiral center can be prepared with high enantiomeric excess through asymmetric transfer hydrogenation (ATH) of ketones. In the reduction step, BCP occupies position distant from η6-arene catalyst. The was applied synthesis analogue antihistamine drug neobenodine.
منابع مشابه
Enantioselective synthesis of alcohols and amines by iridium-catalyzed hydrogenation, transfer hydrogenation, and related processes.
The preparation of chiral alcohols and amines by using iridium catalysis is reviewed. The methods presented include the reduction of ketones or imines by using hydrogen (hydrogenations), isopropanol, formic acid, or formate (transfer hydrogenations). Also dynamic and oxidative kinetic resolutions leading to chiral alcohols and amines are included. Selected literature reports from early contribu...
متن کاملHighly enantioselective asymmetric transfer hydrogenation (ATH) of α-phthalimide ketones.
A mild catalyst system for the synthesis of chiral amino alcohols via asymmetric transfer hydrogenation (ATH) of α-phthalimide ketones has been developed by using a chiral Ru-TsDPEN complex as the catalyst in DMF/MeOH at 40 °C. The reaction exhibits high reaction activity and excellent enantioselectivity where up to 96% yield and 99% ee of the product were obtained.
متن کاملBioinspired enantioselective synthesis of crinine-type alkaloids via iridium-catalyzed asymmetric hydrogenation of enones.
A bioinspired enantioselective synthesis of crinine-type alkaloids has been developed by iridium-catalyzed asymmetric hydrogenation of racemic cycloenones. The method features a biomimetic stereodivergent resolution of the substrates bearing a remote arylated quaternary stereocenter. Using this protocol, 24 crinine-type alkaloids and 8 analogues were synthesized in a concise and rapid way with ...
متن کاملHighly enantioselective synthesis of non-natural aliphatic α-amino acids via asymmetric hydrogenation.
By employing a rhodium-Duanphos complex as the catalyst, β-alkyl (Z)-N-acetyldehydroamino esters were smoothly hydrogenated in a highly efficient and enantioselective way. Excellent enantioselectivities together with excellent yields were achieved for a series of substrates. An efficient approach for the synthesis of the intermediate of the orally administered anti-diabetic drugs Alogliptin and...
متن کاملThe Asymmetric Total Synthesis of (+)- and (-)-Trypargine via Noyori Asymmetric Transfer Hydrogenation
Uma síntese total e eficiente da (+) e (-)-tripargina, alcalóide b-carbolínico isolado da pele da rã africana K. Senegalensis, foi realizada em 6 etapas e 38% de rendimento global, a partir da triptamina, tendo como base a construção do sistema b-carbolínico via reação de BischlerNapieralski e a redução enantiosseletiva do intermediário diidro-b-carbolínico via reação de transferência de hidrog...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
ژورنال
عنوان ژورنال: Organic Letters
سال: 2021
ISSN: ['1523-7060', '1523-7052']
DOI: https://doi.org/10.1021/acs.orglett.1c00889