Enantioselective conjugate addition of boronic acids to enones catalyzed by O-monoacyltartaric acids.
نویسندگان
چکیده
We have found that O-monoacyltartaric acids catalyze asymmetric conjugate addition of boronic acids to enones with good enantioselectivity, and the 3,5-di(tert-butyl)benzoyl group provides the best results among the acyl groups examined.
منابع مشابه
Application of chiral N-tert-butylsulfinyl vinyl aziridines in Rh(I) catalyzed 1,4-addition of aryl boronic acids to cyclic enones.
Chiral N-tert-butylsulfinyl vinyl aziridine ligands prepared from a readily available (R)-tert-butanesulfinamide have been applied in the rhodium-catalyzed asymmetric 1,4-addition of aryl boronic acids to cyclic enones, which gives high yields and excellent enantioselectivities.
متن کاملCatalytic conjugate addition of allyl groups to styryl-activated enones.
Transition-metal-catalyzed conjugate addition of organometallics to activated alkenes is an important process.1 Intense research has focused on the utility of copper2 and rhodium catalysts for asymmetric additions,3 and recent efforts have led to the introduction of effective palladium4 catalysts. Each catalyst system exhibits a unique reactivity profile. The rhodium-catalyzed asymmetric conjug...
متن کاملEnantioselective palladium catalyzed conjugate additions of ortho-substituted arylboronic acids to β,β-disubstituted cyclic enones: total synthesis of herbertenediol, enokipodin A and enokipodin B.
The palladium-catalyzed conjugate addition (Michael addition) of ortho-substituted arylboronic acids to β,β-disubstituted cyclic enones, in particular 3-methyl cyclopent-2-enone and 3-methyl cyclohex-2-enone, is reported. With an achiral bipyridine-based palladium catalyst, good yields are obtained with a variety of ortho-substituted arylboronic acids. In the asymmetric version, good to very hi...
متن کاملPalladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to 5- 6- and 7-Membered β-substituted Cyclic Enones: Enantioselective Construction of All-Carbon Quaternary Stereocenters
The first enantioselective Pd-catalyzed construction of all-carbon quaternary stereocenters via 1,4addition of arylboronic acids to β-substituted cyclic enones is reported. Reaction of a wide range of arylboronic acids and cyclic enones using a catalyst prepared from Pd(OCOCF3)2 and a chiral pyridinooxazoline ligand yields enantioenriched products bearing benzylic stereocenters. Notably, this t...
متن کاملN-Heterocyclic carbene-catalyzed cyclocondensation of 2-aryl carboxylic acids and enones: highly enantioselective synthesis of δ-lactones.
The enantioselective N-heterocyclic carbene-catalyzed [4 + 2] cyclocondensation of 2-aryl carboxylic acids and enones was developed, affording the corresponding chiral δ-lactones in good yields with good diastereo- and high enantioselectivities.
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 46 41 شماره
صفحات -
تاریخ انتشار 2010