Amino Alcohols with Bicyclic Carbon Skeleton. Alternative Functionalization of Nucleophilic Reaction Centers

Kas’yan, L. I.; Golodaeva, E. A.; Kas’yan, A. O.; Isaev, A. K.

doi:10.1023/b:rujo.0000010553.82993.7d

Cited by 4 publications

(7 citation statements)

References 8 publications

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“…The latter procedure was successfully used previously to perform reactions of stereoisomeric 5-aminomethylbicyclo[2.2.1]hept-2-enes 45a and 45b with arenelsulfonyl chlorides [113,117]; however, amino alcohols 128a and 128b gave rise to only 30-40% of sulfonamides 131a and 131b (Scheme 58). Following alternative procedure, the same sulfonamides were obtained in 65-70% yield.…”

Section: Scheme 56mentioning

confidence: 96%

“…Alternative functionalization of nucleophilic centers in cage-like amino alcohols was demonstrated in [62,113]. Treatment of compounds 128a and 128b with hexamethyldisilazane (HMDS) in anhydrous toluene in the presence of chloro(trimethyl)silane at room temperature gave trimethylsilyl ethers 149a and 149b (Scheme 65 [62,113].…”

Section: Scheme 63mentioning

confidence: 98%

“…In some cases, they also contain sterically strained double bond or epoxide ring [62,63,113] in epoxynorbornane fragment which is fairly stable in neutral medium but labile in acid medium [44,13]. Chemoselectivity of transformations of amino alcohols was shown to depend on the reaction medium.…”

Section: Functionalization Of Amino Alcohols With Bicyclic Cage-like mentioning

confidence: 98%

“…Likewise, amino alcohols 128a, 128b, 60a, 60b, 133a, and 133b reacted with substituted (CH 3 , NO 2 ) benzoyl chlorides to give crystalline sulfonamides 134-137 [62,63,113] (Scheme 59). Acylation of amino alcohols in the presence of alkali gave compounds 138-141 [42].…”

Section: Scheme 56mentioning

confidence: 99%

“…Treatment of compounds 128a and 128b with hexamethyldisilazane (HMDS) in anhydrous toluene in the presence of chloro(trimethyl)silane at room temperature gave trimethylsilyl ethers 149a and 149b (Scheme 65 [62,113]. Compounds 149-153 were then subjected to acylation with p-nitrobenzoyl chloride in the absence of a base under mild conditions.…”

Section: Scheme 63mentioning

confidence: 99%

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

Kas’yan

Пальчиков

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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Section: Scheme 56mentioning

confidence: 96%

Section: Scheme 63mentioning

confidence: 98%

Section: Functionalization Of Amino Alcohols With Bicyclic Cage-like mentioning

confidence: 98%

Section: Scheme 56mentioning

confidence: 99%

Section: Scheme 63mentioning

confidence: 99%

See 3 more Smart Citations

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

Kas’yan

Пальчиков

2010

Russ J Org Chem

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Amino Alcohols with Bicyclic Carbon Skeleton. Alternative Functionalization of Nucleophilic Reaction Centers.

et al. 2004

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Bridged compoundsBridged compounds Q 0060 Amino Alcohols with Bicyclic Carbon Skeleton. Alternative Functionalization of Nucleophilic Reaction Centers. -The chemoselective functionalization of the title amino alcohols such as (I) at the nitrogen and oxygen nucleophilic centers is effected by reaction of (I) with electrophilic reagents at the nitrogen atom and via intermediate formation of silyl ethers at the oxygen atom. Oxidation of N,O-bis-acylated amino alcohol (VI) with phthalic anhydride leads to epoxidation and is not accompanied by heterocyclization. The electron density distribution in amino alcohols (I) is calculated by quantum-chemical methods. -(KAS'YAN, L. I.; GOLODAEVA, E. A.; KAS'YAN, A. O.; ISAEV, A. K.; Russ.

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Reaction of bicyclo[2.2.1]hept‐5‐ene‐endo‐2‐ylmethylamine and nitrophenyl glycidyl ethers

Kas’yan

Prid’ma

Пальчиков

et al. 2010

J of Physical Organic Chem

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Reactions of 2‐nitro‐, 4‐nitro‐ and 2,4‐dinitrophenylglycidyl ethers with bicyclo[2.2.1]hept‐5‐ene‐endo‐2‐ylmethylamine in isopropanol have been studied. The mixtures of products were chromatographed on silica gel and eluted with ether or ether/2‐propanol (1:1), the structures of individual products have been confirmed by IR spectra, NMR 1H, 13C spectra, using experiments that involve homonuclear and heteronuclear scalar coupling interactions (COSY, TOCSY, HMQC, HMBC), and mass spectrometry. Amino alcohols as the major products of regioselective aminolysis of epoxides (according to the Krasusky rule) have been obtained. The minor products were the compounds with two hydroxyalkyl fragments at the nitrogen atom. In case of dinitrophenylglycidyl ether, it was the minor product of aryl nucleophilic substitution (SNAr). The abnormal course of aminolysis has been confirmed by the results of quantum‐chemical calculations of activation barries and Free Gibbs energies of the competitive reactions of epoxides (at the B3LYP/6‐311 + G(d,p) level of theory). Copyright © 2010 John Wiley & Sons, Ltd.

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Amino Alcohols with Bicyclic Carbon Skeleton. Alternative Functionalization of Nucleophilic Reaction Centers

Cited by 4 publications

References 8 publications

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

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

Amino Alcohols with Bicyclic Carbon Skeleton. Alternative Functionalization of Nucleophilic Reaction Centers.

Reaction of bicyclo[2.2.1]hept‐5‐ene‐endo‐2‐ylmethylamine and nitrophenyl glycidyl ethers

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