Catalytic Enantioselective Construction of All-Carbon Quaternary Stereocenters Catalytic Enantioselective Construction of All-Carbon Quaternary Stereocenters
نویسندگان
چکیده
SYNTHESIS 2006, No. 3, pp 0369–0396xx.xx.2006 Advanced online publication: 13.01.2006 DOI: 10.1055/s-2006-926302; Art ID: E14205SS © Georg Thieme Verlag Stuttgart · New York Abstract: Catalytic enantioselective construction of all-carbon quaternary stereocenters, i.e. carbon atoms bearing four different carbon substituents, poses a particular challenge in organic synthesis. This review gives a comprehensive account on the currently available methods of the above transformation that afford high enantioselectivities and synthetically useful yields.
منابع مشابه
The Construction of All-Carbon Quaternary Stereocenters by Use of Pd-Catalyzed Asymmetric Allylic Alkylation Reactions in Total Synthesis.
All-carbon quaternary stereocenters have posed significant challenges in the synthesis of complex natural products. These important structural motifs have inspired the development of broadly applicable palladium-catalyzed asymmetric allylic alkylation reactions of unstabilized non-biased enolates for the synthesis of enantioenriched α-quaternary products. This microreview outlines key considera...
متن کاملConstruction of vicinal tertiary and all-carbon quaternary stereocenters via Ir-catalyzed regio-, diastereo-, and enantioselective allylic alkylation and applications in sequential Pd catalysis.
Highly congested vicinal stereocenters comprised of tertiary and all-carbon quaternary centers were generated via Ir-catalyzed asymmetric allylic alkylation of β-ketoesters. These catalytic reactions proceed in excellent yields with a broad scope on either reaction partner and with outstanding regio-, diastereo-, and enantiocontrol. Implementation of a subsequent Pd-catalyzed alkylation affords...
متن کاملPalladium-catalyzed asymmetric decarboxylative cycloaddition of vinylethylene carbonates with Michael acceptors: construction of vicinal quaternary stereocenters.
An efficient method for the diastereo- and enantioselective construction of vicinal all-carbon quaternary stereocenters through palladium-catalyzed decarboxylative cycloaddition of vinylethylene carbonates with activated Michael acceptors was developed. By using a palladium complex generated in situ from [Pd2(dab)3]⋅CHCl3 and a phosphoramidite ligand as a catalyst under mild reaction conditions...
متن کاملEnantioselective synthesis of the 5-6-7 carbocyclic core of the gagunin diterpenoids.
A catalytic enantioselective double allylic alkylation reaction has been employed in the synthesis of the core of the gagunin diterpenoids. Enantioenriched material was advanced in 11 steps to afford the core of the highly oxygenated target, which includes two all-carbon quaternary stereocenters.
متن کاملEnantioselective Construction of Acyclic Quaternary Carbon Stereocenters: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully Substituted Amide Enolates.
We report a divergent and modular protocol for the preparation of acyclic molecular frameworks containing newly created quaternary carbon stereocenters. Central to this approach is a sequence composed of a (1) regioselective and -retentive preparation of allyloxycarbonyl-trapped fully substituted stereodefined amide enolates and of a (2) enantioselective palladium-catalyzed decarboxylative ally...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
دوره شماره
صفحات -
تاریخ انتشار 2006