Enantioselective Three?Component Coupling of Heteroarenes, Cycloalkenes and Propargylic Acetates
نویسندگان
چکیده
Asymmetric coupling proceeds efficiently between propargylic acetates, cycloalkenes and electron-rich heteroarenes including indoles, pyrroles, activated furans thiophenes. 2,3-Disubstituted tetrahydrofurans pyrrolidines are produced in trans configuration excellent enantiomeric ratios. The reaction via Wacker-type attack of nucleophilic on alkenes by allenyl PdII species.
منابع مشابه
Highly enantioselective copper-catalyzed propargylic substitution of propargylic acetates with 1,3-dicarbonyl compounds.
A chiral tridentate ketimine P,N,N-ligand has been successfully applied in the copper-catalyzed enantioselective propargylic substitution of propargylic acetates with a variety of β-dicarbonyl compounds, in which excellent enantioselectivities (up to >99% ee) and high yields have been obtained.
متن کاملEnantioselective Cu-catalyzed decarboxylative propargylic amination of propargyl carbamates
A copper-catalyzed asymmetric propargylic amination with a chiral ketimine P,N,N-ligand that proceeds via decarboxylation of propargyl carbamates has been developed. The reaction can be performed under the mild condition for a broad range of substrates, providing the corresponding propargylic amines in high yields and with up to 97% ee. This reaction represents a new and facile access to optica...
متن کاملCopper-catalyzed propargylic substitution of dichloro substrates: enantioselective synthesis of trisubstituted allenes and formation of propargylic quaternary stereogenic centers.
An easy and versatile Cu-catalyzed propargylic substitution process is presented. Using easily prepared prochiral dichloro substrates, readily available Grignard reagents together with catalytic amount of copper salt and chiral ligand, we accessed a range of synthetically interesting trisubstituted chloroallenes. Substrate scope and nucleophile scope are broad, providing generally high enantios...
متن کاملCopper(II)-mediated dehydrogenative cross-coupling of heteroarenes.
Cu(OAc)(2)-mediated dehydrogenative cross-coupling between two heteroarenes has been realized in the absence of any other additive. A mechanism involving a formal Cu(II) to Cu(0) route by convergent disproportionation of the copper mediator is proposed and has been evidenced by copper mirror formation during the reaction. This synthetic protocol provides a concise and "green" access to unsymmet...
متن کاملDesilylation-Activated Propargylic Transformation: Enantioselective Copper-Catalyzed [3+2] Cycloaddition of Propargylic Esters with β-Naphthol or Phenol Derivatives.
A copper-catalyzed asymmetric [3+2] cycloaddition of 3-trimethylsilylpropargylic esters with either β-naphthols or electron-rich phenols has been realized and proceeds by a desilylation-activated process. Under the catalysis of Cu(OAc)2⋅H2O in combination with a structurally optimized ketimine P,N,N-ligand, a wide range of optically active 1,2-dihydronaphtho[2,1-b]furans or 2,3-dihydrobenzofura...
متن کاملذخیره 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: Angewandte Chemie
سال: 2021
ISSN: ['1521-3773', '1433-7851', '0570-0833']
DOI: https://doi.org/10.1002/anie.202014781