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Carman, Raymond M.; Handley, Paul

doi:10.1071/ch01168

Cited by 11 publications

(12 citation statements)

References 27 publications

(95 reference statements)

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“…For the structure elucidation of the marsupial dihydroxylated products of 1,8‐cineole detoxication (see section 4), Carman et al 9. 20–22, 32, 37 synthesized a number of dihydroxy derivatives of 1,8‐cineole ( 13 – 20 ) and some of the corresponding hydroxycineolic acids, starting from known optically pure hydroxylated α‐terpineol analogues.…”

Section: Synthesis Of Oxidized Derivatives Of 18‐cineolementioning

confidence: 99%

1,8‐Cineole: Chemical and Biological Oxidation Reactions and Products

Azerad

2014

ChemPlusChem

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ChemPlusChem 2014, 79, 634 -655 635 CHEMPLUSCHEM REVIEWS www.chempluschem.org son. Cineolic acids were generally identified as their methyl esters and sometimes (hydroxycineolic acids) doubly derivatized to form trimethylsilyl ether derivatives of hydroxyl groups before GC-MS analysis.When a sufficient amount of pure product is obtained, 1 H and 13 C NMR spectroscopy are essential for the full identification of isomers, making use of the downfield shift of the proton(s) gem to the OH group(s) and the 3 J coupling constants observed between the vicinal hydrogen atoms. However, the information obtained is frequently obscured in the d = 1-Robert Azerad was born in Oran (Algeria) in 1938. Educated first in Algiers then in Paris (France), he was trained in biochemistry and chemistry and obtained his PhD in Physical Sciences at Paris-Sud University in 1967 with Prof. E. Lederer. He has held positions at the

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Section: Synthesis Of Oxidized Derivatives Of 18‐cineolementioning

confidence: 99%

1,8‐Cineole: Chemical and Biological Oxidation Reactions and Products

Azerad

2014

ChemPlusChem

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“…Epoxidation of 2 with t -BuOOH in the presence of vanadyl acetylacetonate (VO(acac) 2 ) as catalyst furnished epoxide 19 in a stereospecific reaction [35,42,43,44]. Since our earlier results clearly demonstrated that substituents at nitrogen of aminodiols exerted definite influence on the efficiency of their catalytic activity, aminodiol library 20 – 23 was prepared by aminolysis of 19 with different primary amines and LiClO 4 as catalyst [17,41,45,46], whereas exposure of 19 to NaOH furnished 29 with retention of stereochemistry [47].…”

Section: Resultsmentioning

confidence: 99%

“…Stereospecific epoxidation of allylic diol 3 with t -BuOOH and VO(acac) 2 was successfully applied to prepare epoxy diol 31 [35,43,44] (Scheme 3). The relative configuration of epoxide 31 was determined by means of NOESY experiments.…”

Section: Resultsmentioning

confidence: 99%

Stereoselective Synthesis and Investigation of Isopulegol-Based Chiral Ligands

Lê

Szilasi

Volford

et al. 2019

IJMS

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A library of isopulegol-based bi-, tri- and tetrafunctional chiral ligands has been developed from commercially available (−)-isopulegol and applied as chiral catalysts in the addition of diethylzinc to benzaldehyde. Michael addition of primary amines towards α-methylene-γ-butyrolactone, followed by reduction, was accomplished to provide aminodiols in highly stereoselective transformations. Stereoselective epoxidation of (+)-neoisopulegol, derived from natural (−)-isopulegol, and subsequent oxirane ring opening with primary amines afforded aminodiols. The regioselective ring closure of N-substituted aminodiols with formaldehyde was also investigated. Hydroxylation of (+)-neoisopulegol resulted in diol, which was then transformed into aminotriols by aminolysis of its epoxides. Dihydroxylation of (+)-neoisopulegol or derivatives with OsO4/NMO gave neoisopulegol-based di-, tri- and tetraols in highly stereoselective reactions. The antimicrobial activity of aminodiol and aminotriol derivatives as well as di-, tri- and tetraols was also explored. In addition, structure–activity relationships were examined by assessing substituent effects on the aminodiol and aminotriol systems.

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“…[10] Epoxidation of 6 in dry toluene in the presenceo fv anadyl acetylacetonate [VO(acac) 2 ]a sacatalyst gave am ixture of 7 and 8.N ote that 8 exists as a4:1 mixture of two diastereomers (Scheme 1). [36][37][38] In addition, it is interesting that the ratio of 7 and 8 was dependent on the temperature.…”

Section: Introductionmentioning

confidence: 99%

Regio‐ and Stereoselective Synthesis of Bicyclic Limonene‐Based Chiral Aminodiols and Spirooxazolidines

Lê

Csámpai

Fülöp

et al. 2018

Chemistry A European J

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A library of monoterpene-based aminodiols was synthesized and applied as chiral catalysts in the addition of diethylzinc to benzaldehyde. The reduction of a bicyclic α-methylene ketone, derived from natural (-)-limonene followed by epoxidation, gave the key epoxy alcohol intermediate. Ring opening of the oxirane ring with primary amines induced by lithium perchlorate afforded the required aminodiols. Substituent-dependent ring closure of the secondary aminodiols with formaldehyde resulted in both spirooxazolidines and a fused 1,3-oxazine. Cyclization reactions of the studied aminodiols, resulting in spirocyclic oxazolidines and an isomeric perhydro-1,3-oxazine-fused compound along with the possible iminium intermediates, were analyzed by a systematic series of comparative DFT models performed at the B3LYP/6-31+G(d,p) level of theory.

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Untitled

Cited by 11 publications

References 27 publications

1,8‐Cineole: Chemical and Biological Oxidation Reactions and Products

1,8‐Cineole: Chemical and Biological Oxidation Reactions and Products

Stereoselective Synthesis and Investigation of Isopulegol-Based Chiral Ligands

Regio‐ and Stereoselective Synthesis of Bicyclic Limonene‐Based Chiral Aminodiols and Spirooxazolidines

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