P,S-Bidentate Phosphoramidites with (Ra)-BINOL Core in Palladium-Catalyzed Asymmetric Allylic Substitution

نویسندگان

چکیده

Abstract New P , S -bidentate phosphoramidite ligands, including these having a stereogenic phosphorus atom in the 1,3,2-dioxaphosphepine ring, have been synthesized on basis of ( R )-BINOL and its adamantanyl derivatives. With their participation Pd-catalyzed asymmetric allylic alkylation E )-1,3-diphenylallyl acetate with dimethyl malonate amination pyrrolidine involving ligands afforded selectivity up to 84 75% ee respectively.

برای دانلود باید عضویت طلایی داشته باشید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Palladium Catalyzed Allylic Substitution of Acyloxypyrrolinones

Enantiomerically pure alkoxypyrrolinones have been shown to be facile building blocks for a variety of stereoselective syntheses involving Diels-Alder cycloadditions , 1,3dipolar reactions, conjugate additions, and acyliminium ion intermediates. In particular the application in the asymmetric synthesis of alkaloids based on N-acyliminium ion chemistry is of current interest. For example, (R)-1-...

متن کامل

Palladium-catalyzed asymmetric synthesis of allylic fluorides.

The enantioselective fluorination of readily available cyclic allylic chlorides with AgF has been accomplished using a Pd(0) catalyst and Trost bisphosphine ligand. The reactions proceed with unprecedented ease of operation for Pd-mediated nucleophilic fluorination, allowing access to highly enantioenriched cyclic allylic fluorides that bear diverse functional groups. Evidence that supports a m...

متن کامل

Palladium-catalyzed Substitution Reaction of Allylic Derivatives with Tinacetylene.

The substitution reaction of allylic derivatives (acetate, carbonate, and chloride) with tinacetylene proceeded in the presence of palladium as a catalyst to give a product having a 1-ene-4-yne system.

متن کامل

Design of bifunctional chiral phenanthroline ligand with Lewis basic site for palladium-catalyzed asymmetric allylic substitution.

Conceptually new bifunctional chiral ligands were developed. The axially chiral N,N-bidentate phenanthroline ligand (S)-1 was found to be effective for Pd-catalyzed asymmetric allylic substitution of allyl acetate and dialkyl malonate. The intramolecular Lewis basic group from the hydroxybinaphthyl structure of (S)-1 played a pivotal role in the high reactivity and enantioselectivity.

متن کامل

Chalcogen-Containing Oxazolines in the Palladium-Catalyzed Asymmetric Allylic Alkylation

The search for new ligands in asymmetric catalysis is a field of continuing interest. To facilitate practical applications, new ligands should be easy to prepare from simple and easily available starting materials. In this context, the use of chiral nitrogen compounds bearing an organochalcogen moiety and their metal complexes have gained increased importance in the field of asymmetric catalysi...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

ژورنال

عنوان ژورنال: Russian Journal of General Chemistry

سال: 2022

ISSN: ['1070-3632', '1608-3350']

DOI: https://doi.org/10.1134/s1070363222120088