Palladium-catalyzed asymmetric 1,6-addition of diarylphosphines to α,β,γ,δ-unsaturated sulfonic esters: controlling regioselectivity by rational selection of electron-withdrawing groups.
نویسندگان
چکیده
Palladium-catalyzed asymmetric 1,6-addition of diarylphosphines to electron-deficient dienes was developed through rational selection of electron-withdrawing groups on the dienes. Various chiral allylic phosphine derivatives were synthesized in good yields with high enantioselectivity (up to 96% ee).
منابع مشابه
Palladium catalyzed asymmetric hydrophosphination of α,β- and α,β,γ,δ-unsaturated malonate esters - efficient control of reactivity, stereo- and regio-selectivity.
Both PC-cyclometalated and PCP-pincer type palladium catalysts have recently been found to be robust and efficacious catalysts for the asymmetric P-H addition reaction involving activated olefins. Our studies on the asymmetric P-H addition of diphenylphosphine to malonate ester and α,β,γ,δ-alkylidenemalonate ester revealed for the first time that the catalyst choice can have a dramatic impact i...
متن کاملElectronic tuning of chiral diene ligands in iridium-catalyzed asymmetric 1,6-addition of arylboroxines to δ-aryl-α,β,γ,δ-unsaturated ketones.
Asymmetric addition of arylboroxines to δ-aryl-α,β,γ,δ-unsaturated ketones proceeded in the presence of an iridium catalyst coordinated with a chiral diene ligand to give high yields of δ-diaryl ketones with very high enantioselectivity.
متن کاملPeptide-catalyzed consecutive 1,6- and 1,4-additions of thiols to α,β,γ,δ-unsaturated aldehydes.
Regio- and enantioselective addition of thiols to α,β,γ,δ-unsaturated aldehydes was performed with a resin-supported peptide catalyst. It was shown that a 1,4-adduct was generated mainly at the initial stage of the reaction, and this was eventually converted to a thermodynamically stable 1,6- and 1,4-diadduct through retro-addition/addition reactions.
متن کاملCopper-catalyzed cascade reactions of α,β-unsaturated esters with keto esters
A copper-catalyzed cascade reaction of α,β-unsaturated esters with keto esters is reported. It features a copper-catalyzed reductive aldolization followed by a lactonization. This method provides a facile approach to prepare γ-carboxymethyl-γ-lactones and δ-carboxymethyl-δ-lactones under mild reaction conditions.
متن کاملMicrowave assisted Pd(OAc)2-catalyzed chemoselective reduction of aryl α,β-unsaturated esters with triethylsilane
< p>In this communication, we have reported that the Pd(OAc)2–Et3SiH-DMF system promotes the microwave-assisted chemoselective reduction of aryl α,β-unsaturated esters in good yields. The protocol affords a convenient reduction of aryl-conjugated double bonds even in presence of other functional groups like esters, phenols, and ethers.
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 50 6 شماره
صفحات -
تاریخ انتشار 2014