Expedient synthesis of cyclopropane alpha-amino acids by the catalytic asymmetric cyclopropanation of alkenes using iodonium ylides derived from methyl nitroacetate.
نویسندگان
چکیده
A highly enantioselective (up to 97.5% ee) and diastereoselective (95:5 dr trans/cis) Cu(I)-catalyzed cyclopropanation of alkenes using phenyliodonium ylide generated in situ from iodosobenzene and methyl nitroacetate is reported. The cyclopropanation took place with high enantioselectivity for a wide range of alkenes, and the reaction was performed at room temperature. 1-Nitrocyclopropyl esters are versatile building blocks to access the corresponding cyclopropane amino esters and aminocyclopropanes in two and three steps, respectively, from commercially available products.
منابع مشابه
A Crystallization-Induced Asymmetric Transformation using Racemic Phenyl Alanine Methyl Ester Derivatives as Versatile Precursors to Prepare Amino Acids
L-Tyrosine and L-Dopa are the precursors in the biological synthesis of amine neurotransmitters. On the other hand, phenylalanine as an aromatic amino acid (AAA) is a precursor in the synthesis of L-Tyrosine and L-Dopa. For some substrates such as amino acids, resolution by the formation of diastereomers offers an attractive alternative. Among different methods in this case, crystallization-ind...
متن کاملA temporary stereocentre approach for the asymmetric synthesis of chiral cyclopropane-carboxaldehydes.
A novel way of combining chiral auxiliaries and substrate directable reactions is described that employs a three-step sequence of aldol/cyclopropanation/retro-aldol reactions for the asymmetric synthesis of enantiopure cyclopropane-carboxaldehydes. In the first step, reaction of the boron enolate of (S)-N-propionyl-5,5-dimethyl-oxazolidin-2-one with a series of alpha,beta-unsaturated aldehydes ...
متن کاملNickel(ii)-catalyzed enantioselective cyclopropanation of 3-alkenyl-oxindoles with phenyliodonium ylide via free carbene† †Electronic supplementary information (ESI) available. CCDC 1038443 and 1038445. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5sc03658e Click here for additional data file. Click here for additional data file.
The catalytic asymmetric cyclopropanation of a C]C double bond provides efficient access to optically active cyclopropane derivatives that are essential motifs in natural products and valuable building blocks for various transformations. Chiral transition-metal-catalyzed carbene transfer, such as that using Cu(I)-, Rh(II)-, Ru(II)-, and Co(II)-complexes with diazo compounds, permits such cylcop...
متن کاملAsymmetric synthesis of cyclopropanes and dihydrofurans based on phosphine oxide chemistry.
The asymmetric synthesis of gamma-azido trans-cyclopropyl ketones is accomplished via a short, simple and efficient sequence. The cyclopropanation step is achieved by an intramolecular nucleophilic ring closure, with a diphenylphosphinate leaving group, to give trans-cyclopropane exclusively. beta-Keto-diphenylphosphine oxides cyclise to form optically active dihydrofurans. All possible diaster...
متن کاملThree-component procedure for the synthesis of new chiral spirooxindolopyrrolizidines via catalytic highly enantioselective 1,3-dipolar cycloaddition
The catalytic highly regio-, diastereo-, and enantioselective synthesis of a small library of spiropyrrolizidineoxindolesvia a four-component 1,3-dipolar cycloaddition reaction of azomethine ylides, derived from isatin, with electron-deficient dipolarophilewas described. The process occurs at room temperature in aqueous ethanol as a green solvent and in the presence of a bidendatebis(imine)–Cu(...
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:
- Journal of the American Chemical Society
دوره 127 51 شماره
صفحات -
تاریخ انتشار 2005