Transition metal-catalyzed addition reactions of arylboronic acids with alkyl 2-formylbenzoates: efficient access to chiral 3-substituted phthalides.
نویسندگان
چکیده
Transition metal-catalyzed addition of arylboronic acids to 2-formylbenzoates afforded 3-substituted phthalides. By using SPINOL-based phosphites as ligands, a Rh(I)-catalyzed asymmetric version of such an addition reaction was achieved.
منابع مشابه
Enantioselective addition of arylboronic acids to methyl 2-formylbenzoates by using a ruthenium/Me-BIPAM catalyst for synthesis of chiral 3-aryl-isobenzofuranones.
Ruthenium/Me-BIPAM-catalyzed asymmetric addition of arylboronic acids to methyl 2-formylbenzoates afforded chiral 3-aryl-isobenzofuranones. [RuCl2(p-cymene)]2/Me-BIPAM and RuCl2(PPh3)3/Me-BIPAM catalyst systems tolerate a variety of functional groups and give high yields with high enantioselectivities.
متن کاملPalladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to 5- 6- and 7-Membered β-substituted Cyclic Enones: Enantioselective Construction of All-Carbon Quaternary Stereocenters
The first enantioselective Pd-catalyzed construction of all-carbon quaternary stereocenters via 1,4addition of arylboronic acids to β-substituted cyclic enones is reported. Reaction of a wide range of arylboronic acids and cyclic enones using a catalyst prepared from Pd(OCOCF3)2 and a chiral pyridinooxazoline ligand yields enantioenriched products bearing benzylic stereocenters. Notably, this t...
متن کاملRhodium-Catalyzed Addition of Arylboronic Acids to N-Sulfonyl Aldimines
The addition of arylboronic acids, ArB(OH)2, to N-phenylsulfonyl aldimines, RCH=NSO2Ph (R=alkyl, aryl, 1-alkenyl), giving R(Ar)CHNHSO2Ph was carried out at 95 °C in the presence of a rhodium catalyst. [Rh(cod)(MeCN)2]BF4 (3 mol%) was found to be the best catalyst for aryl aldimines and Rh(acac)(coe)2/i-Pr3P for alkyl and 1-alkenyl aldimines. The analogous reactions of arylboronic esters, such a...
متن کاملRu/Me-BIPAM-catalyzed asymmetric addition of arylboronic acids to aliphatic aldehydes and α-ketoesters.
A ruthenium-catalyzed asymmetric arylation of aliphatic aldehydes and α-ketoesters with arylboronic acids has been developed, giving chiral alkyl(aryl)methanols and α-hydroxy esters in good yields. The use of a chiral bidentate phosphoramidite ligand (Me-BIPAM) achieved excellent enantioselectivities.
متن کاملRhodium-catalyzed asymmetric 1,4-addition reactions of aryl boronic acids with nitroalkenes: reaction mechanism and development of homogeneous and heterogeneous catalysts† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc03025h
Asymmetric 1,4-addition reactions with nitroalkenes are valuable because the resulting chiral nitro compounds can be converted into various useful species often used as chiral building blocks in drug and natural product synthesis. In the present work, asymmetric 1,4-addition reactions of arylboronic acids with nitroalkenes catalyzed by a rhodium complex with a chiral diene bearing a tertiary bu...
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 46 17 شماره
صفحات -
تاریخ انتشار 2010