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Kas’yan, L. I.; Tarabara, I. N.; Kas’yan, A. O.

doi:10.1023/a:1015338305344

Cited by 10 publications

(4 citation statements)

References 3 publications

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“…The importance of the steric factor is obvious from the absence of the heterocyclization in the epoxidation reactions of compounds 118, 119 [121,122] and the lack of the formation of the azabrendane system at the oxidation of more bulky but also more conformationally labile camphorsulfonamide 120 (Scheme 41) [123].…”

Section: Heterocyclization Of Epoxide Derivatives Of Framework Aminesmentioning

confidence: 99%

Azacycloalkanes from epoxides and aziridines

2011

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Section: Heterocyclization Of Epoxide Derivatives Of Framework Aminesmentioning

confidence: 99%

Azacycloalkanes from epoxides and aziridines

2011

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“…It was rationalized in terms of steric hindrances to attack by nucleophile from the rear (endo) side of the carbon skeleton according to the S N 2 mechanism. Compounds 57 and 58 were described in [63,64], and amino alcohol 59 was reported in [65]. These amino alcohols were synthesized under similar conditions, namely by stirring p-nitrophenyloxirane (50) with the corresponding amines in isopropyl alcohol at room temperature.…”

Section: Synthesis Of Amino Alcohols From Bi-and Polycyclic Cage-likementioning

confidence: 99%

Cage-like amino alcohols. synthesis, reactions, and application

Kas’yan

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2010

Russ J Org Chem

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The review analyzes methods for the synthesis of amino alcohols containing cage-like norbornene, norbornane, and adamantane fragments. Such reactions of amino alcohols as selective functionalization of hydroxy and amino groups, as well as heterocyclizations with formation of nitrogen-and oxygen-containing heterocycles, are considered. Biological activity of cage-like amino alcohols and their derivatives and their use as ligands in catalytic asymmetric syntheses are discussed.

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“…The spectra of X-XVI contained two new signals, an unresolved four-proton multiplet at δ 2.21-2.28 ppm (CH 2 CH 2 ) and a diffuse signal at δ 7.60-7.70 ppm (exchangeable protons of the carboxy Amine VII [14] was synthesized according to modified procedure [15] from the cyclopentadiene adduct with acrolein. The spectra of X-XVI contained two new signals, an unresolved four-proton multiplet at δ 2.21-2.28 ppm (CH 2 CH 2 ) and a diffuse signal at δ 7.60-7.70 ppm (exchangeable protons of the carboxy Amine VII [14] was synthesized according to modified procedure [15] from the cyclopentadiene adduct with acrolein.…”

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confidence: 99%

10.1007/s11178-008-3005-4

2010

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Succinic anhydride reacted with cage-like amines {bicyclo[2.2.1]hept-5-en-exo-and -endo-2-ylmethanamines, 2-(bicyclo[2.2.1]hept-5-en-endo-2-yl)ethanamine, exo-5,6-epoxybicyclo[2.2.1]heptan-exo-2-ylmethanamine, tetracyclo[6.2.1.1 3,6 .0 2,7 ]dodec-9-en-endo-4-ylmethanamine, 1-(bicyclo[2.2.1]heptan-2-yl)ethanamine, and 4-azatricyclo[5.2.1.0 2,6 ]dec-8-ene} to give the corresponding amido acids having a cage-like fragment. The latter were converted into carboximides by the action of hexamethyldisilazane in boiling benzene in the presence of zinc(II) chloride and then into epoxy derivatives. The structure of the newly synthesized compounds was confirmed by IR and NMR spectroscopy.

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Cited by 10 publications

References 3 publications

Azacycloalkanes from epoxides and aziridines

Azacycloalkanes from epoxides and aziridines

Cage-like amino alcohols. synthesis, reactions, and application

10.1007/s11178-008-3005-4

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