Three-component, room temperature crotylation catalyzed by solid-supported Brønsted acid: enantioselective synthesis of homoallylic carbamates.
نویسندگان
چکیده
[reaction: see text] A heterogeneous, three-component crotylation of in situ generated N-acyl iminium ions has been developed. This reaction proceeds under ambient temperature in MeCN and is catalyzed by macroporous polystyrene-bound sulfonic acid (MP-TsOH). Workup is accomplished by filtration, upon which the catalyst is recoverable. A range of homoallylic amine equivalents have been prepared from the corresponding aldehydes, carbamates, and chiral (E)-crotylsilanes in a highly stereoselective manner.
منابع مشابه
Brønsted acidic ionic liquid ([BMIm]HSO4) as an efficient catalysts for the one-pot synthesis of 2H-indazolo[2,1-b]phthalazine-trione derivatives
The Brønsted acidic ionic liquid ([BMIm]HSO4) catalyzed three-component synthesis of 2H-indazolo[2,1-b]phthalazine-trione derivatives at room temperature. The integrity of the ionic liquid remains reasonably unchanged when it is separated from the reaction mixture by water extraction, as it can be recycled several times without any loss of activity in each of the title syntheses. The products a...
متن کاملSynthesis of Bis-4-hydroxycoumarins via a Multi Component Reaction Using Silica Boron-sulfuric Acid Nanoparticles (SBSANs) as an Efficient Heterogeneous Solid Acid Catalyst
The silica boron sulfuric acid nanoparticles (SBSANs) as an efficient heterogeneous solid acid catalyst with both Brønsted and Lewis acidic sites catalyzed the preparation of bis-4-hydroxycoumarin derivatives using reaction of aldehydes and 4-hydroxycoumarin under mild and solvent-free condition at room temperature. This new and efficient methodology has advantages in comparison with currently ...
متن کاملBrønsted acidic ionic liquid ([BMIm]HSO4) as an efficient catalysts for the one-pot synthesis of 2H-indazolo[2,1-b]phthalazine-trione derivatives
The Brønsted acidic ionic liquid ([BMIm]HSO4) catalyzed three-component synthesis of 2H-indazolo[2,1-b]phthalazine-trione derivatives at room temperature. The integrity of the ionic liquid remains reasonably unchanged when it is separated from the reaction mixture by water extraction, as it can be recycled several times without any loss of activity in each of the title syntheses. The products a...
متن کاملChiral Brønsted acid-catalyzed allylboration of aldehydes.
The catalytic enantioselective allylation of aldehydes is a long-standing problem of considerable interest to the chemical community. We disclose a new high-yielding and highly enantioselective chiral Brønsted acid-catalyzed allylboration of aldehydes. The reaction is shown to be highly general, with a broad substrate scope that covers aryl, heteroaryl, alpha,beta-unsaturated, and aliphatic ald...
متن کاملThree-Component and Click Strategy for Synthesis of β-Hydroxy 1,4-Disubstituted 1,2,3-Triazoles Derivatives Catalyzed by 1,4-Dihydroxyanthraquinone-copper(II) Complex onto Nano AlPO4
In this work, copper(II) heterogeneous nanocatalyst supported on modified AlPO4 (Cu(II)-DA@Nano AlPO4) was used for the synthesis of some biological active heterocyclic molecules, particularly for the efficient conversion of a wide range of non-activated terminal alkynes to β-hydroxy 1,4-disubstituted 1,2,3-triazolethrough a three-component “click” reaction at room temperature in water. The reg...
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:
- Organic letters
دوره 7 21 شماره
صفحات -
تاریخ انتشار 2005