Quinine-thiourea catalyzed enantioselective hydrophosphonylation of trifluoromethyl 2(1H)-quinazolinones.
نویسندگان
چکیده
An organocatalytic enantioselective addition reaction of cyclic ketoimines with phosphites has been developed for the first time. The process, catalyzed by Soós' quinine thiourea, affords synthetically and medicinally interesting enantioenriched trifluoromethyl dihydroquinazolinones in high yields and with high enantioselectivities.
منابع مشابه
Expeditious diastereoselective construction of a thiochroman skeleton via a cinchona alkaloid-derived catalyst.
An example of diastereoselective and enantioselective synthesis of thiochroman derivatives through a sulfa-Michael-Michael cascade sequence is disclosed. This is a significant complement of the quinine-thiourea catalyzed sulfa-Michael-Michael cascade reaction. The densely functionalized target thiochromans were obtained in high diastereoselectivities, and with high to excellent enantioselectivi...
متن کاملNHCs Catalyzed Hydrophosphonylation of α-Ketoesters and α-Trifluoromethyl Ketones
N-Heterocyclic carbenes catalyzed hydrophosphonylation reaction of α-ketoesters and α-trifluoromethyl ketones was developed. Under the catalysis of 10 mol% IPr, α-ketoesters or α-trifluoromethyl ketones reacted with dialkyl phosphites to provide quaternary α-hydroxyphosphonates in good to excellent yield.
متن کاملA Highly Diastereoselective and Enantioselective Phase-Transfer Catalyzed Epoxidation of β-Trifluoromethyl-β,β-disubstituted Enones with H2O2
Trifluoromethylated organic compounds, especially chiral quaternary alcohols bearing trifluoromethyl group are of important intermediates in drugs, agrochemicals and etc.An efficient epoxidation of β-CF3-β,β-disubstituted unsaturated ketones (6) has been developed with environmental benign hydrogen peroxide as the oxidant and F5-substituted chiral qua...
متن کاملEnantioselective organocatalytic oxa-Michael addition of oximes to β-CF3-β-disubstituted nitroalkenes: efficient synthesis of β-amino-α-trifluoromethyl alcohols.
An enantioselective oxa-Michael addition of oximes to β-CF3-β-disubstituted nitroalkenes catalyzed by a chiral bifunctional cinchona alkaloid-based thiourea has been developed. A variety of trifluoromethylated oxime ethers possessing a tetrasubstituted carbon stereocenter were obtained in good yields with high enantioselectivities.
متن کاملCatalytic highly enantioselective transfer hydrogenation of β-trifluoromethyl nitroalkenes. An easy and general entry to optically active β-trifluoromethyl amines.
In the presence of a thiourea catalyst, β-CF3 nitroalkenes react with Hantzsch esters in a highly enantioselective fashion, giving a broad range of β-CF3 amine precursors with a tertiary stereocentre at the β-position. This reaction represents the first general catalytic enantioselective approach to this important class of β-CF3 amines.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Chemical communications
دوره 49 9 شماره
صفحات -
تاریخ انتشار 2013