An N-linked bidentate phosphoramidite ligand (N-Me-BIPAM) for rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated ketones.
نویسندگان
چکیده
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.
منابع مشابه
Ru/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 کاملChiral N-tert-butanesulfinyl α,β-unsaturated ketimine: a simple and highly effective olefin/sulfinimide hybrid ligand for asymmetric 1,4-additions.
One novel type of chiral olefin/sulfinimide hybrid ligands has been developed through a simple one-step condensation of α,β-unsaturated ketones with tert-butanesulfinamide and utilized successfully for rhodium-catalyzed asymmetric conjugated additions to furnish the desired adducts in high yields with excellent ee's.
متن کاملEnantioselective rhodium-catalyzed addition of arylboronic acids to trifluoromethyl ketones.
The catalytic asymmetric 1,2-addition of a series of arylboronic acids to 2,2,2-trifluoroacetophenones is described with high isolated yields (up to 96%) and good enantioselectivities (up to 83% ee) using a rhodium(I)/phosphoramidite catalyst.
متن کاملChiral amidophosphane-rhodium(i)-catalyzed asymmetric conjugate arylation of acyclic enones with arylboronic acids.
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 re...
متن کاملRhodium(I)-catalyzed 1,4-conjugate arylation toward β-fluoroalkylated electron-deficient alkenes: a new entry to a construction of a tertiary carbon center possessing a fluoroalkyl group.
Treatment of β-fluoroalkylated-α,β-unsaturated ketones with 1.2 equiv. of various arylboronic acids in the presence of 5 mol% of [Rh(COD)(2)]BF(4) and 6 mol% of (S)-BINAP in toluene/H(2)O (v/v = 4/1) at the reflux temperature for 3 h gave the corresponding Michael adducts in high yields with over 90% enantioselectivity. Though other electron-deficient alkenes, such as vinylsulfone and vinylphos...
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:
- Molecules
دوره 18 1 شماره
صفحات -
تاریخ انتشار 2012