Iridium/copper-cocatalyzed asymmetric ring opening reaction of azabenzonorbornadienes with amines.
نویسندگان
چکیده
A combination of iridium/copper associated with (R)-Difluorphos catalyst for the asymmetric ring opening reaction of azabenzonorbornadienes with amines was developed, which afforded chiral trans-vicinal diamines in 80-97% yields with 93-95% enantioselectivities.
منابع مشابه
Iridium-catalyzed asymmetric ring-opening of azabicyclic alkenes with alcohols.
A novel asymmetric ring-opening reaction of N-substituted azabenzonorbornadienes with a wide variety of substituted benzyl alcohols and the addition reaction of N-substituted azabenzonorbornadienes with thiols are reported, affording the corresponding 1,2-trans-alkoxyamino products in moderate yields with excellent enantioselectivities (up to 94% ee) and the corresponding thiol addition product...
متن کاملIridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with secondary amine nucleophiles
Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with various aliphatic and aromatic secondary amines are reported for the first time. The reaction gave the corresponding trans-1,2-dihydronaphthalenol derivatives in good yields with moderate enantioselectivities in the presence of 2.5 mol % [Ir(COD)Cl](2) and 5 mol % bisphosphine ligand (S)-p-Tol-BINAP. The trans-confi...
متن کاملCatalytic asymmetric ring-opening of cyclopentadiene–heterodienophile cycloadducts with organometallic reagents*
An unprecedented catalytic asymmetric ring-opening of easily accessible 2,3-heterosubstituted norbornenes with hard alkyl metals (R-M), is able to give a practical regioand stereoselective access to hetero-functionalized alkyl cyclopentenes in an enantioenriched form. The copper-catalyzed desymmetrization reaction with trialkylaluminums of sterically hindered and rigid, trior tetracyclic Diels–...
متن کاملIridium-Catalyzed Asymmetric Ring-Opening of Oxabenzonorbornadienes with N-Substituted Piperazine Nucleophiles.
Iridium-catalyzed asymmetric ring-opening of oxabenzonorbornadienes with N-substituted piperazines was described. The reaction afforded the corresponding ring-opening products in high yields and moderate enantioselectivities in the presence of 2.5 mol % [Ir(COD)Cl]₂ and 5.0 mol % (S)-p-Tol-BINAP. The effects of various chiral bidentate ligands, catalyst loading, solvent, and temperature on the ...
متن کاملEfficient ruthenium and copper cocatalzyed five-component coupling to form dipropargyl amines under mild conditions in water.
Dipropargyl amines are synthesized by a double direct alkynylation of primary followed by secondary imines formed in situ during an efficient, five-component, one-pot coupling reaction cocatalyzed by ruthenium and copper in water.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- Organic & biomolecular chemistry
دوره 13 31 شماره
صفحات -
تاریخ انتشار 2015