Search results for "enantioselective synthesis"

ChemInform Abstract: Enantioselective Synthesis of 4-Substituted Dihydrocoumarins Through a Zinc Bis(hydroxyamide)-Catalyzed Conjugate Addition of Te…

2013

Terminal alkynes (II) react with coumarins (I) in the presence of diethylzinc and chiral bis(hydroxyamide) ligands to give enantiopure dihydrocoumarins (III) substituted with an alkynyl group in C(4) position in good enantioselectivities.

ChemInform Abstract: Enantiocontrol in the Intermolecular Cyclopropanation Reaction Catalyzed by Dirhodium(II) Complexes with ortho-Metalated Aryl Ph…

2010

(P) and (M) dirhodium(II) complexes with ortho-metalated aryl phosphines are assessed as chiral catalysts in the enantioselective cyclopropanation of styrenes by ethyl diazoacetate; enantioselectivities up to 91% and up to 87%, respectively, for cis- and trans-2-arylcyclopropanecarboxylates are observed.

ChemInform Abstract: Glycosylation-Induced Asymmetric Synthesis of 1-Substituted Tetrahydroisoquinolines.

2008

ChemInform Abstract: Aza-Henry Reaction of Isatin Ketimines with Methyl 4-Nitrobutyrate en Route to Spiro[piperidine-3,3′-oxindoles].

2016

A new enantioselective route to spiro[piperidine-3,3′-oxindoles] from isatin ketimines is described. The aza-Henry reaction of N-Boc-isatin ketimines with methyl 4-nitrobutyrate in the presence of a Ph2BOX-CuBr2 complex provided the corresponding nitro amino esters with good diastereoselectivity and excellent enantioselectivity (up to >99% ee). The aza-Henry adducts were transformed into spiro[piperidine-3,3′-oxindoles] after reduction of the nitro group to oxime, and cleavage of the N-Boc group and lactamisation.

ChemInform Abstract: Highly Enantioselective Aza-Henry Reaction with Isatin N-Boc Ketimines.

2014

The asymmetric aza-Henry reaction of isatin N-Boc-ketimines (I) with nitromethane in the presence of a Cu-Ph-box complex leads to a series of N-Boc-protected nitroamines (III) with high enantioselectivity in most cases.

Organocatalytic enantioselective aza-Friedel–Crafts reaction of 2-naphthols with benzoxathiazine 2,2-dioxides

2015

An organocatalytic enantioselective aza-Friedel–Crafts addition of 2-naphthols to benzoxathiazine 2,2-dioxides is described using a quinine-derived bifunctional catalyst. The method allows the use of a wide range of aromatic compounds as nucleophiles, including 1-naphthol and sesamol, and benzoxathiazines 2,2-dioxides, expanding the existing state of the art enantioselective synthesis of aminomethylnaphthol derivatives.

ChemInform Abstract: Organocatalytic Enantioselective Aza-Friedel-Crafts Reaction of 2-Naphthols with Benzoxathiazine 2,2-Dioxides.

2015

An organocatalytic enantioselective aza-Friedel–Crafts addition of 2-naphthols to benzoxathiazine 2,2-dioxides is described using a quinine-derived bifunctional catalyst. The method allows the use of a wide range of aromatic compounds as nucleophiles, including 1-naphthol and sesamol, and benzoxathiazines 2,2-dioxides, expanding the existing state of the art enantioselective synthesis of aminomethylnaphthol derivatives.

A New Tandem Cross Metathesis-Intramolecular Aza-Michael Reaction for the Synthesis of α,α-Difluorinated Lactams

2012

A new tandem cross metathesis–intramolecular aza-Michael­ reaction in which an α,α-difluorinated amide serves as a source of nucleophilic nitrogen is described. This process gives rise to a new family of fluorinated γ- and δ-lactams. The tandem protocol is catalyzed by the Hoveyda–Grubbs second-generation ruthenium catalyst with titanium(IV) tetraisopropoxide as a co-catalyst and it is highly efficient when conjugated ketones are used as the Michael acceptors. With conjugated esters, however, it is necessary to perform a step-by-step procedure in which the cyclization event is activated by the addition of a base. An asymmetric version of the process is also evaluated.

ChemInform Abstract: Cooperative Assistance in Bifunctional Organocatalysis: Enantioselective Mannich Reactions with Aliphatic and Aromatic Imines.

2013

both of which contain a thiourea moiety (Scheme 1).The catalysts are capable of deprotonating suitable nucleo-philes, such as activated carbonyl compounds. This proton-transfer reaction generates an ion pair, which is composed ofthe protonated catalyst and the anionic nucleophile interact-ing through hydrogen bonds. At least one of the NH moietiesin the protonated catalyst is involved in activating theelectrophilic reaction partner.

α-Amido Sulfones as Imine Precursors in Enantioselective Nucleophilic Additions

2013

Alicia Monleon was born in Valencia, Spain, in 1985. She obtained her B.Sc. and M.Sc. degrees in Chemistry from the University of Valencia, where she is currently pursuing her Ph.D. under the supervision of Prof. Jose Ramon Pedro and Prof. Gonzalo Blay. She has carried out pre-doctoral stays at the University of Aachen, Germany, with Prof. C. Bolm and at the University of Strathclyde, UK, with Dr. E. Hevia. Departament de Quimica Organica, Facultat de Quimica, Universitat de Valencia, C/ Dr. Moliner 50, 46100 Burjassot, Spain E-mail: alicia.monleon@uv.es