82227-98-3

Upstream product

• 111423-98-4 (+/-)-N-benzyl isonitramine 
• 925422-81-7 2-(toluene-4-sulfonyl)-2-aza-spiro[5.5]undecan-7-one 
• 675-20-7 piperidin-2-one 
• 925422-76-0 3-(5-trimethylsilylpent-4-ynyl)piperidin-2-one 
• 925422-32-8 5-(pent-4-ynyl)-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridine 
• 925422-36-2 1-methyl-7-(toluene-4-sulfonyl)-7-aza-spiro[4.5]dec-1-ene 
• 925422-79-3 3-[3-acetyl-1-(toluene-4-sulfonyl)piperidin-3-yl]propionaldehyde 
• 925422-80-6 2-(toluene-4-sulfonyl)-2-aza-spiro[5.5]undec-8-en-7-one 
• 925422-78-2 1-(toluene-4-sulfonyl)-5-(5-trimethylsilylpent-4-ynyl)-1,2,3,4-tetrahydropyridine 
• 66927-74-0 5-bromo-1-(trimethylsilyl)pentyne 
• 42894-09-7 ethyl 1-(2-cyanoethyl)-2-oxocyclohexanecarboxylate 
• 92423-37-5 2-(3-aminopropyl)cyclohexanone ethylene acetal 
• 120210-97-1 (R)-2-Benzyl-11-(tert-butyl-dimethyl-silanyloxy)-2-aza-spiro[5.5]undec-7-ene 
• 42894-18-8 6-(2-cyano-ethyl)-1,4-dioxa-spiro[4.5]decane-6-carboxylic acid ethyl ester 

Downstream Products

• 81149-24-8 N-methyl-O-tosylisonitramine 
• 81149-27-1 (S)-8-[1-Phenyl-meth-(E)-ylidene]-2-aza-spiro[5.5]undecan-7-one 

Relevant academic research and scientific papers

Enantioselective Total Synthesis of Nitraria Alkaloids: (+)-Nitramine, (+)-Isonitramine, (-)-Isonitramine, and (-)-Sibirine via Asymmetric Phase-Transfer Catalytic α-Allylations of α-Carboxylactams

Many optically active 2-azaspirocyclic structures have frequently been found in biologically active natural products. In particular, Nitraria alkaloids, (+)-nitramine, (+)-isonitramine, (-)-isonitramine, and (-)-sibirine, have stereogenicity on their quat

Highly enantioselective total synthesis of (+)-isonitramine

A new efficient enantioselective synthetic method of (+)-isonitramine is reported. (+)-Isonitramine was obtained in 12 steps (98% ee and 43% overall yield) from δ-valerolactam via enantioselective phase-transfer catalytic alkylation, Dieckman condensation

Platinum(II)-catalyzed cyclizations forming quaternary carbon centers, using enesulfonamides, enecarbamates, or enamides as nucleophiles

(Chemical Equation Presented) Cyclic enesulfonamides, enecarbamates, or enamides tethered to an alkyne cyclize readily with use of platinum(II) chloride. This reaction generates quaternary-substituted carbon centers within simple spiro-fused or more compl

Synthesis of racemic nitramine, isonitramine and sibirine

Condensation of enol ether 6 with methyl vinyl ketone led easily to ketoaldehyde 7 whose cyclisation afforded the azaspiranic enone 8, a key intermediate for the synthesis of the title alkaloids.

An asymmetric synthesis of (+)-isonitramine by 'triple allylic strain-controlled' intramolecular S(N)2' alkylation

The spirocyclic alkaloid (+)-isonitramine (1) has been synthesized in a stereoselective manner utilizing a novel 'triple allylic strain-controlled' intramolecular lactam enolate S(N)2' alkylation.

Stereoselective Synthesis of (+/-)-Isonitramine and (+/-)-Sibirine

Spirocyclic alkaloids, (+/-)-isonitramine and (+/-)-sibirine were synthesized in high overall yields via a chemoselective reduction by Hantzsch ester (HEH), a coenzyme NADH model compound.

SYNTHESIS OF (+/-)-NITRAMINE, (+/-)-ISONITRAMINE AND (+/-)-SIBIRINE VIA DIELS-ALDER REACTIONS

Diels-Alder reactions with N-protected methyleneglutarimides are used to construct the spiro-framework during the synthesis of the title alkaloids.

Synthesis of (+/-)-Nitramine and (+/-)-Isonitramine

The alkaloids (+/-)-nitramine (1; R=H) and (+/-)-isonitramine (2; R=H) have been synthesized, employing an intramolecular Mannich rection to set up the spirocyclic ring system.

ASYMMETRIC SYNTHESIS XV: ENANTIOSPECIFIC SYNTHESIS OF (+) AND (-) ISONITRAMINES FROM A COMMON CHIRAL INTERMEDIATE.

The enantiospecific synthesis of (+) and (-) isonitramines 7 has been achieved from a common chiral intermediate 5; this key compound was formed by condensation of two molar equivalents of glutaraldehyde with one mole of (-) phenylglycinol.