Journal ArticleDOI
BF3 x OEt2-mediated highly regioselective S(N)2-type ring-opening of N-activated aziridines and N-activated azetidines by tetraalkylammonium halides.
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TLDR
An easy diastereoselective route toward substituted chiral N-tosylaziridines has been developed and the mechanism of ring-opening via S(N)2 pathway has been confirmed by the formation of chiral haloamines.Abstract:
A highly regioselective Lewis acid-mediated S(N)2-type ring-opening of N-sulfonylaziridines and azetidines with tetraalkylammonium halides in CH(2)Cl(2) solution to afford 1,2- and 1,3-haloamines in excellent yields is described. An easy diastereoselective route toward substituted chiral N-tosylaziridines has been developed. The mechanism of ring-opening via S(N)2 pathway has been confirmed by the formation of chiral haloamines with excellent er and dr. Chloroamines obtained from 2,3-disubstituted aziridines were converted to the chiral N-tosylamines via radical dehalogenation.read more
Citations
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Journal ArticleDOI
Regioselectivity in the ring opening of non-activated aziridines.
Sonja Stanković,Matthias D'hooghe,Saron Catak,Heesung Eum,Michel Waroquier,Veronique Van Speybroeck,Norbert De Kimpe,Hyun-Joon Ha +7 more
TL;DR: This overview should allow chemists to gain insight into the factors governing the regioselectivity in aziridinium ring openings and inherent structural features such as the nature of the C2 aziridine substituent and the natureof the electrophile and the nucleophile.
Journal ArticleDOI
Catalytic asymmetric cross-aza-benzoin reactions of aliphatic aldehydes with N-Boc-protected imines.
Daniel A. DiRocco,Tomislav Rovis +1 more
TL;DR: In a study of aza-Breslow intermediates, acetic acid was found to be a competent catalyst in regenerating the active carbene and addition of these carbene species to an iminium salt is facile, leading to a stable intermediate.
Journal ArticleDOI
Enantioselective N ? H Insertion Reaction of α‐Aryl α‐Diazoketones: An Efficient Route to Chiral α‐Aminoketones
TL;DR: The insertion reaction provides a new access route to diverse chiral α-aminoketones, which are versatile building blocks in organic synthesis, with fast reaction rates, good yields and high enantioselectivity under mild and neutral conditions.
Journal ArticleDOI
Cinchona Alkaloid Amide Catalyzed Enantioselective Formal [2+2] Cycloadditions of Allenoates and Imines: Synthesis of 2,4-Disubstituted Azetidines†
TL;DR: The quinidine-amide (1)-catalyzed [2+2] cycloaddition between N-sulfonylimines and alkyl 2,3-butadienoate afforded the (R)-azetidines 4 in excellent yields and enantioselectivities.
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Ring Opening/C–N Cyclization of Activated Aziridines with Carbon Nucleophiles: Highly Diastereo- and Enantioselective Synthesis of Tetrahydroquinolines
TL;DR: A simple strategy for the synthesis of substituted tetrahydroquinolines through regio- and stereoselective ring opening of N-tosyl aziridines with carbon nucleophiles generated from 2-(bromoaryl)acetonitriles followed by palladium-catalyzed intramolecular C-N cyclization is reported in excellent yields and stereodelectivity.
References
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Journal ArticleDOI
Catalytic enantioselective addition to imines.
Shu Kobayashi,Haruro Ishitani +1 more
TL;DR: Shū Kobayashi was born in 1959 in Tokyo, Japan and studied chemistry at the University of Tokyo and received his Ph.D. in 1988 (Professor T. Mukaiyama), and received the first Springer Award in Organometallic Chemistry in 1997.
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Chiral Aziridines—Their Synthesis and Use in Stereoselective Transformations
TL;DR: Chiral bisaziridines can be used as ligands for transition metals, and applications in the challenging field of enantioselective catalysis can be envisioned as discussed by the authors.
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Additions of Organometallic Reagents to C=N Bonds: Reactivity and Selectivity
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Aziridines: epoxides’ ugly cousins?
TL;DR: The similarities and differences between oxiranes and their nitrogenated analogues are summarized, concentrating on the underlying properties of aziridines and recent developments in their chemistry.