Chiral amidophosphane-rhodium(i)-catalyzed asymmetric conjugate arylation of acyclic enones with arylboronic acids.
نویسندگان
چکیده
A catalytic asymmetric conjugate arylation of acyclic alpha,beta-unsaturated ketones with arylboronic acids was catalyzed by 3 mol% of chiral amidomonophosphane 1-rhodium(I) in the presence of potassium hydroxide in a mixture of 1,4-dioxane and water at 70 degrees C to afford 1,4-conjugate arylated acyclic ketones with high enantiomeric excess in high chemical yield. Thirteen examples of the reaction demonstrate the general applicability of the catalytic system.
منابع مشابه
An N-linked bidentate phosphoramidite ligand (N-Me-BIPAM) for rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated ketones.
A new bidentate phosphoramidite (N-Me-BIPAM) based on Shibasaki's N-linked BINOL was synthesized. This ligand appears to be highly effective for rhodium-catalyzed asymmetric conjugated addition of arylboronic acids to α,β-unsaturated enones. The reaction of ortho-substituted arylboronic acid with acyclic and cyclic enones provides the corresponding products in good yields and enantioselectivities.
متن کاملThe concise synthesis of chiral tfb ligands and their application to the rhodium-catalyzed asymmetric arylation of aldehydes.
New C2-symmetric tetrafluorobenzobarrelene ligands were prepared and applied successfully to the rhodium-catalyzed asymmetric addition of arylboronic acids to aromatic aldehydes giving chiral diarylmethanols in high yield with high enantioselectivity.
متن کاملRhodium/phosphoramidite-catalyzed asymmetric arylation of aldehydes with arylboronic acids.
Phosphoramidites are effective chiral ligands in the rhodium catalyzed addition of arylboronic acids to aldehydes providing up to 75% enantioselectivity and up to 96% isolated yield.
متن کاملRhodium/diene-catalyzed asymmetric arylation of N-sulfonyl indolylimines: a new access to highly optically active α-aryl 3-indolyl-methanamines.
A new and efficient method for the preparation of highly enantiomerically enriched α-aryl 2- or 3-indolyl-methanamines by rhodium-catalyzed asymmetric arylation of N-sulfonyl indolylimines with arylboronic acids using chiral bicyclo[3.3.0] diene was developed.
متن کاملA second-generation ligand for the enantioselective rhodium-catalyzed addition of arylboronic acids to alkenylazaarenes.
A 2,4,6-trialkylanilide-containing chiral diene has been identified as a superior ligand for the enantioselective rhodium-catalyzed arylation of alkenylazaarenes with arylboronic acids.
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 & pharmaceutical bulletin
دوره 57 9 شماره
صفحات -
تاریخ انتشار 2009