0000000000116331
AUTHOR
Lode De Munck
showing 12 related works from this author
Catalytic Enantioselective Aza-Reformatsky Reaction with Cyclic Imines
2016
A catalytic highly enantioselective aza-Reformatsky reaction with cyclic aldimines and ketimines for the synthesis of chiral b-amino esters with good yields and excellent enantioselectivities is reported.Areadily available diaryl prolinol is used as a chiral ligand, ZnMe2 as a zinc source and ethyl iodoacetate as reagent in the presence of air atmosphere. The reaction with cyclic ketimines generates a quaternary stereocenter with excellent levels of enantioselectivity. Furthermore, five-membered N-sulfonyl ketimines were used as electrophiles with good enantiomeric excesses, under the optimized reaction conditions. Moreover, several chemical transformations were performed with the chiral b-…
Catalytic Asymmetric Reactions Involving the Seven-Membered Cyclic Imine Moieties Present in Dibenzo[b,f][1,4]oxazepines
2017
The dibenzo[b,f][1,4]oxazepine scaffold is a privileged structure in medicinal chemistry that displays a wide variety of biological and pharmacological activities. However, catalytic asymmetric methodologies for the synthesis of chiral dibenzo[b,f][1,4]oxazepine derivatives are scarce in the literature. This microreview presents an overview of enantioselective reactions in which these cyclic seven-membered imines are used as electrophiles, including their substrate scope, limitations and application to the synthesis of related compounds.
Enantioselective alkynylation of benzo[e][1,2,3]-oxathiazine 2,2-dioxides catalysed by (R)-VAPOL-Zn complexes: synthesis of chiral propargylic cyclic…
2015
[EN] (R)-VAPOL-Zn(II) complexes catalysed the enantioselective addition of terminal alkynes to cyclic benzoxathiazine 2,2-dioxides, providing the corresponding chiral propargylic sulfamidates with high yields (up to 93%) and good enantiomeric excesses (up to 87%).
Enantioselective addition of Et2Zn to seven‐membered cyclic imines catalyzed by a (R)-VAPOL-Zn(II) complex
2017
Various substituted dibenzo[b,f][1,4]oxazepines underwent an enantioselective alkylation with Et2Zn catalyzed by a (R)-VAPOL-Zn(II) complex. The corresponding chiral 11-ethyl-10,11-dihydrodibenzo[b,f][1,4]oxazepine derivatives were obtained with good yields and moderate enantioselectivities. This represents the first example of enantioselective addition of Et2Zn to cyclic aldimines.
Diarylprolinol as a Ligand for Enantioselective Alkynylation of Cyclic Imines
2017
An easily accessible prolinol derived ligand, (S)-bis(3,5-bis(trifluoromethyl)phenyl)(pyrrolidin-2-yl)methanol, has been efficiently applied in the catalytic enantioselective addition of terminal alkynes to cyclic imines using dimethylzinc (Me2Zn) under mild reaction conditions. The developed catalytic system led to chiral propargylic sulfamidates with high yields (up to 97%) and excellent enantioselectivities (up to 97% ee).
Catalytic enantioselective aza-Reformatsky reaction with seven-membered cyclic imines dibenzo[b,f][1,4]oxazepines
2017
A catalytic enantioselective aza-Reformatsky reaction is reported with cyclic dibenzo[b,f][1,4]oxazepines and ethyl iodoacetate leading to the synthesis of chiral ethyl 2-(10,11-dihydrodibenzo[b,f][1,4]oxazepin-11-yl)acetate derivatives with excellent yields and high enantioselectivities (up to 98% yield and 97 : 3 er) using a readily available diaryl prolinol L4 as the chiral ligand and Me2Zn as the zinc source under an air atmosphere. Furthermore, different transformations were carried out with the corresponding chiral β-amino esters, preserving in all cases the optical purity.
Synthesis of Multisubstituted 1,4-Dihydrobenzoxazin-2-ones through a One-Pot Nucleophilic N-Alkylation/C-Alkylation of Cyclic α-Imino Esters
2017
A nucleophilic N-alkylation of 2-oxobenzoxazine-2-carboxylates with organozinc reagents with good selectivities and in moderate to good yields is described. Moreover, the synthesis of multisubstituted 1,4-dihydrobenzoxazine-2-ones bearing a tetrasubstituted carbon atom via a one-pot N-alkylation/C-alkylation reactions is reported.
Catalytic Asymmetric Reactions Involving the Seven-Membered Cyclic Imine Moieties Present in Dibenzo[b,f][1,4]oxazepines
2018
The dibenzo[b,f][1,4]oxazepine scaffold is a privileged structure in medicinal chemistry that displays a wide variety of biological and pharmacological activities. However, catalytic asymmetric methodologies for the synthesis of chiral dibenzo[b,f][1,4]oxazepine derivatives are scarce in the literature. This microreview presents an overview of enantioselective reactions in which these cyclic seven-membered imines are used as electrophiles, including their substrate scope, limitations and application to the synthesis of related compounds.
Alquinilación y alquilación enantioselectivas de iminas cíclicas
2017
Mirando la base de datos de la FDA, se observa que casi 60% de los fármacos formados por moléculas pequeñas contienen al mínimo un heterociclo nitrogenado. Además, en muchos de los casos, se puede encontrar un estereocentro (terciario o cuaternario) en el carbono en la posición α al nitrógeno. Una de las maneras de obtener este tipo de compuestos es por una adición nucleofílica enantioselectiva de reactivos organometalicos a iminas cíclicas, lo cual se supone un gran desafío por la baja reactividad del carbono azometínico. En esta Tesis, se ha llevado a cabo la adición enantioselectiva de alquinos terminales a iminas cíclicas de tipo 2,2-dióxido benzoxatiazinas. La reacción fue catalizada p…
CCDC 1401764: Experimental Crystal Structure Determination
2015
Related Article: Lode De Munck, Alicia Monleón, Carlos Vila, M. Carmen Muñoz, José R. Pedro|2015|Org.Biomol.Chem.|13|7393|doi:10.1039/C5OB01012H
CCDC 1503457: Experimental Crystal Structure Determination
2016
Related Article: Lode De Munck, Carlos Vila, M. Carmen Muñoz, José R. Pedro|2016|Chem.-Eur.J.|22|17590|doi:10.1002/chem.201604606
CCDC 1530500: Experimental Crystal Structure Determination
2017
Related Article: Lode De Munck, Verena Sukowski, Carlos Vila, M. Carmen Muñoz, José R. Pedro|2017|Org.Chem.Front.|4|1624|doi:10.1039/C7QO00329C