Highly regioselective ring-opening coupling of diarylmethylenecyclopropa[b]naphthalenes with Grignard reagents.
نویسندگان
چکیده
Highly regioselective ring-opening coupling reactions of diarylmethylenecyclopropa[b]naphthalenes with Grignard reagents have been developed, which provide differently substituted β-vinylic naphthalenes in moderate to excellent yields.
منابع مشابه
A ligand-controlled switch of regioselectivity in ring-opening coupling of diarylmethylenecyclopropa[b]naphthalenes with Grignard reagents.
A ligand-controlled regioselectivity switch of ring-opening coupling reaction of diarylmethylenecyclopropa[b]naphthalenes with Grignard reagents providing differently substituted β-vinylic naphthalenes in moderate to excellent yields was reported: when Pd(OAc)2 was used, the aromatic group from the Grignard reagent regioselectively coupled to the naphthyl ring after the ring-opening of three-me...
متن کاملSynthesis of γ-hydroxypropyl P-chirogenic (±)-phosphorus oxide derivatives by regioselective ring-opening of oxaphospholane 2-oxide precursors
The synthesis of P-chirogenic (±)-phosphine oxides and phosphinates via selective nucleophilic ring opening of the corresponding oxaphospholanes is described. Two representative substrates: the phosphonate 2-ethoxy-1,2-oxaphospholane 2-oxide and the phosphinate 2-phenyl-1,2-oxaphospholane 2-oxide were reacted with various Grignard reagents to produce a single alkyl/aryl product. These products ...
متن کاملOne-pot synthesis of highly regioselective β-azido alcohols catalyzed by Brønsted acidic ionic liquids
In this protocol, 3-(2-carboxybenzoyl)-1-methyl-1H-imidazol-3-ium chloride [Cbmim]Cl and sulfonic acid functionalized pyridinium chloride [pyridine-SO3H]Cl as a new, reusable, and green Brønsted acidic ionic liquid (BAIL) catalyst were synthesized and successfully used for the one-pot ring opening of epoxide with sodium azide (NaN3) in water at room temperature. Epoxides under ring-opening easi...
متن کاملDirected functionalization of 1,2-dihydropyridines: stereoselective synthesis of 2,6-disubstituted piperidines.
A practical and highly stereoselective approach to access 2,6-disubstituted piperidines using an amidine auxiliary is reported. Following the diastereoselective addition of Grignard reagents at the 2-position of an activated pyridinium salt, the amidine group directs a regioselective metalation at the 6-position, enabling further functionalization. A subsequent electrophilic quench or a Negishi...
متن کاملMagnesium Oxide Nanoparticles for Catalytic Synthesis of 2-Substituted Alcohols from Regioselective Ring Opening of Epoxides in Water
Epoxides undergo regioselective ring opening with various nucleophiles using catalytic amount of nano magnesium oxide and water as solvent under mild reaction conditions. The remarkable features of this method are improved yields, high regioselectivity, and green chemistry agreement.
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 42 شماره
صفحات -
تاریخ انتشار 2013