The SAMP-/RAMP-hydrazone methodology in asymmetric synthesis

Job, Andreas; Janeck, Carsten F.; Bettray, Wolfgang; Peters, René; Enders, Dieter

doi:10.1016/s0040-4020(02)00080-7

Cited by 363 publications

(157 citation statements)

References 418 publications

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“…The chiral hydrazone 7 was prepared by condensation of aldehyde 5 with chiral auxiliary SAMP 6. In order to prepare the 1,3-anti system, we tried to apply the usual Enders asymmetric alkylation conditions, 4 To remove the chiral auxiliary, we used ozonolysis followed by treatment with NaBH 4 , in order to avoid any epimerization.…”

Section: Resultsmentioning

confidence: 99%

Studies toward total synthesis of tautomycetin

Sant’Ana¹,

Fiqueiredo²,

Campagne³

et al. 2013

Proceedings of the 14th Brazilian Meeting on Organic Synthesis Proceedings

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Section: Resultsmentioning

confidence: 99%

Studies toward total synthesis of tautomycetin

Sant’Ana¹,

Fiqueiredo²,

Campagne³

et al. 2013

Proceedings of the 14th Brazilian Meeting on Organic Synthesis Proceedings

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“…Some of compounds containing hydrazone unit were found to have antibacterial, antitumor and other activities [6]. In addition hydrazones have been used to build chiral centers and special skeletons in organic synthesis [7]. The crystal structure of the title compoud is built up by only the C 13 H 13 N 5 O 6 molecules.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of (Z)-1-(2,4-dinitrophenyl)-2-(3-methyl-2- nitrocyclohex-2-enylidene)hydrazine, C13H13N5O6

Zhu¹,

Guo²,

Yang³

2010

Zeitschrift Für Kristallographie - New Crystal Structures

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C 13 H 13 N 5 O 6 ,monoclinic, P12 1 /c1(no. 14), a =14.501(2) Å, b =6.362(1) Å, c =17.166(2) Å, b =110.913(9)°, Source of materialThe stock solutions was prepared by dissolving 0.5 mmol (Z)-1-(2,4-dinitrophenyl)-2-(3-methylcyclohex-2-enylidene)-hydrazine in 100 ml dry CH 2 Cl 2 .NOwas produced by the reaction of 1mol H2SO4 solution with saturated NaNO2 aqueous solution. The former was added to the latter, which was stirred under argon atmosphere. NO was carried by argon and purified by passing it through aseries of scrubbing bottles containing 4MKOH, distilled water, and CaCl 2 in turn. The bottles were under an argon atmosphere. The purified NO was bubbled through ad egassed stirred stock solution at room temperature for an appropriate time. After completing of the reaction, as indicated by TLC, the reaction mixture was dried with unhydrous MgSO 4,c oncentrated in vacuum, then recrystallized from hexane/ethyl acetate. Experimental detailsHydrogen atoms were positioned geometrically, with d(C-H) = 0.93 (aromatic) and 0.96 Å (methyl), and constrained to ride on their parent atoms with U iso (H) = xU eq (C), where x =1.2 (aromatic) and x =1.5 (methyl), respectively.

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“…In recent years, some of them and their complexes were found to have anti-cancer properties. In particular, hydrazones have been used to build chiral configurations and certain specific skeletons [7,8]. The crystal structure of the title compound is built up by only the C14H11N5O7 molecules (figure, top), in which all bond lengths are in normal ranges.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of (E)-4-methoxy-nitrophenoiie N-(2,4-dinitrophenyl) hydrazone, C14H11N5O7

Zhao¹

2006

Zeitschrift Für Kristallographie - New Crystal Structures

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The SAMP-/RAMP-hydrazone methodology in asymmetric synthesis

Cited by 363 publications

References 418 publications

Studies toward total synthesis of tautomycetin

Studies toward total synthesis of tautomycetin

Crystal structure of (Z)-1-(2,4-dinitrophenyl)-2-(3-methyl-2- nitrocyclohex-2-enylidene)hydrazine, C13H13N5O6

Crystal structure of (E)-4-methoxy-nitrophenoiie N-(2,4-dinitrophenyl) hydrazone, C14H11N5O7

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