169764-16-3Relevant articles and documents
Visible Light-Mediated Synthesis of Enantiopure γ-Cyclobutane Amino and 3-(Aminomethyl)-5-phenylpentanoic Acids
Kerres, Sabine,Plut, Eva,Malcherek, Simon,Rehbein, Julia,Reiser, Oliver
supporting information, (2019/02/07)
A visible light-mediated [2+2] photocycloaddition of amide-linked dienes using [Ir(dtb-bpy)(dF(CF3)ppy)2]PF6 as triplet sensitizer was applied to generate a variety of N-tert-butyl, N-benzyl- and N-tert-butoxycarbonyl-protected 3-azabicyclo[3.2.0]heptan-2-ones in good yields and with good diastereoselectivity. Density functional theory calculations shed light on the conformational prerequisites for the [2+2] photocycloaddition. The bicyclic key structures could be readily transformed into γ-cyclobutane amino acids. For the obtained racemic 3-phenyl-2-aminocyclobutane-1-carboxylic acid the resolution with chiral oxazolidin-2-one is demonstrated to allow access to both enantiomers. Alternatively, a chiral auxiliary approach led as well to the enantiomerically pure target compound. Finally, the synthesis of either enantiomer of 3-(aminomethyl)-5-phenylpentanoic acid, the racemate being described as an anticonvulsant, is described.
Visible Light-Mediated Synthesis of Enantiopure g-Cyclobutane Amino and 3-(Aminomethyl)-5-phenylpentanoic Acids
Kerres, Sabine,Plut, Eva,Malcherek, Simon,Rehbein, Julia,Reiser, Oliver
supporting information, p. 1400 - 1407 (2019/10/28)
A visible light-mediated [2+2] photocycloaddition of amide-linked dienes using [Ir(dtb-bpy)(dF(CF3)ppy)2]PF6 as triplet sensitizer was applied to generate a variety of N-tert-butyl, N-benzyl- and N-tert-butoxycarbonyl-protected 3-aza-bicyclo[3.2.0]heptan-2-ones in good yields and with good diastereoselectivity. Density functional theory calculations shed light on the conformational prerequisites for the [2+2] photocycloaddition. The bicyclic key structures could be readily transformed into g-cyclobutane amino acids. For the obtained racemic 3-phenyl-2-aminocyclobu-tane-1-carboxylic acid the resolution with chiral oxazolidin-2-one is demonstrated to allow access to both enantiomers. Alternatively, a chiral auxiliary approach led as well to the enantiomerically pure target compound. Finally, the synthesis of either enantiomer of 3-(aminomethyl)-5-phenylpentanoic acid, the racemate being described as an anticonvulsant is described.
FENDILINE DERIVATIVES AND METHODS OF USE THEREOF
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Page/Page column 76, (2014/03/25)
Disclosed herein are novel derivatives of fendiline, including compounds of the formula: wherein the variables are defined herein. Also provided are pharmaceutical compositions, kits and articles of manufacture comprising these derivative compounds. Methods and intermediates useful for making the derivatives, and methods of using the derivatives, for example, for the inhibition of K-Ras plasma membrane localization, and compositions thereof, including for the treatment of cancer, are also provided.
Tsuji-trost N-allylation with allylic acetates by using a cellulose-palladium catalyst
Vaddula, Buchi Reddy,Saha, Amit,Varma, Rajender S.,Leazer, John
supporting information, p. 6707 - 6709 (2013/01/15)
Allylic amines were synthesized by a simple procedure using a biodegradable and easily recyclable heterogeneous cellulose-Pd catalyst through N-allylation of primary and secondary amines. The scope of this protocol includes aliphatic and benzylamines with substituted and unsubstituted allyl acetates and culminates in high yield syntheses. The highlights of the protocol include a ligand-free reaction, simple workup, and catalyst recyclability. Allylic amines were synthesized by N-allylation of primary and secondary amines through a simple and easy procedure involving the use of a heterogeneous cellulose-Pd catalyst; aliphatic and benzylamines underwent facile reaction with substituted and unsubstituted allyl acetates in high yields. Copyright
Novel Tandem Conjugate Addition-Ramberg-B?cklund Rearrangements
Evans, Paul,Taylor, Richard J. K.
, p. 1043 - 1044 (2007/10/03)
A novel tandem process is reported for the preparation of allylic amines, ethers and sulfides from α-bromo-α,β-unsaturated sulfones; this process is believed to proceed via an initial conjugate addition followed by proton exchange and Ramberg-Ba?cklund rearrangement.
