Enantioselective synthesis of chiral phosphonylated 2,3-dihydrofurans by copper catalyzed asymmetric formal [3+2] cycloaddition of propargylic esters with β-keto phosphonates
نویسندگان
چکیده
منابع مشابه
Desilylation-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 کاملEnantioselective chlorination and fluorination of beta-keto phosphonates catalyzed by chiral Lewis acids.
The direct chiral Lewis acidic enantioselective chlorination and fluorination of beta-keto phosphonates is presented; the chlorination proceeds in high yields and with up to 94% ee using NCS as the chloro source, while the fluorination with (PhSO2)2NF (NFSI) gives the optically active alpha-fluoro-beta-keto phosphonates in moderate to good yields and with up to 91% ee.
متن کاملCopper-catalyzed cascade reactions of α,β-unsaturated esters with keto esters
A copper-catalyzed cascade reaction of α,β-unsaturated esters with keto esters is reported. It features a copper-catalyzed reductive aldolization followed by a lactonization. This method provides a facile approach to prepare γ-carboxymethyl-γ-lactones and δ-carboxymethyl-δ-lactones under mild reaction conditions.
متن کاملHighly Enantioselective Hydrogenation of a-Keto Esters Catalyzed by Ru-Tunephos Complexes Highly Enantioselective Hydrogenation of a-Keto Esters
SYNLETT 2006, No. 8, pp 1169–117215.05.2006 Advanced online publication: 10.03.2006 DOI: 10.1055/s-2006-932461; Art ID: W30605ST © Georg Thieme Verlag Stuttgart · New York Abstract: Various enantiomerically pure a-hydroxy esters were synthesized by asymmetric hydrogenation of a-keto esters catalyzed by Ru-Cn-Tunephos complex. Up to 97.1% ee has been achieved for both a-aryl and a-alkyl substitu...
متن کاملEnantioselective copper-catalyzed decarboxylative propargylic alkylation of propargyl β-ketoesters with a chiral ketimine P,N,N-ligand.
The first enantioselective copper-catalyzed decarboxylative propargylic alkylation has been developed. Treatment of propargyl β-ketoesters with a catalyst, prepared in situ from [Cu(CH3 CN)4 BF4 ] and a newly developed chiral tridentate ketimine P,N,N-ligand under mild reaction conditions, generates β-ethynyl ketones in good yields and with high enantioselectivities without requiring the pregen...
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ژورنال
عنوان ژورنال: Chinese Journal of Catalysis
سال: 2016
ISSN: 1872-2067
DOI: 10.1016/s1872-2067(16)62488-9