40179-50-8

Upstream product

• 122-04-3 4-nitro-benzoyl chloride 
• 494-52-0 Anabasine 
• 31944-77-1 (2S)-N-benzyl-2-(3-pyridyl)-piperidine 
• 141120-60-7 (2S)-N-benzyl-2-(3-pyridyl)-4-piperidinone 
• 141120-48-1 (2S)-N-benzyl-2,3-dihydro-2-(3-pyridyl)-4-pyridone 
• 141120-47-0 benzyl-pyridin-3-ylmethylene-amine 
• 122294-65-9 2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-2-((S)-7-pyridin-3-yl-1,4-dithia-8-aza-spiro[4.5]dec-8-yl)-tetrahydro-pyran-3-yl ester 
• 121675-93-2 2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-2-((S)-4-oxo-3,4,5,6-tetrahydro-2H-[2,3']bipyridinyl-1-yl)-tetrahydro-pyran-3-yl ester 
• 121675-95-4 2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-2-(S)-3,4,5,6-tetrahydro-2H-[2,3']bipyridinyl-1-yl-tetrahydro-pyran-3-yl ester 
• 337974-57-9 (S)-8-((S)-1-Phenyl-ethyl)-7-pyridin-3-yl-1,4-dithia-8-aza-spiro[4.5]decane 
• 337974-55-7 (2S)-N-[(1S)-1-phenylethyl]-2-(3-pyridyl)-4-piperidone 
• 337974-58-0 (2S)-N-[(1S)-1-phenylethyl]-2-(3-pyridyl)-4-piperidine 
• 337974-47-7 5-[(4'-methylphenyl)sulfonyl]-1-(3'-pyridyl)-1-penten-3-one 
• 500-22-1 3-pyridinecarboxaldehyde 

Downstream Products

• 494-52-0 Anabasine 

Relevant academic research and scientific papers

Enantioselective syntheses of 2-alkyl-, 2,6-dialkylpiperidines and indolizidine alkaloids through diastereoselective Mannich-Michael reactions

Aldimines of 2,3,4,6-tetra-O-pivaloyl-β-D-galactosylamine react with 1-methoxy-3-trimethylsilyloxybuta-1,3-diene in a Mannich-Michael condensation reaction sequence to give 2-substituted N-galactosyl-5,6-dehydropiperidin-4-ones 3 with high diastereoselectivity. The X-ray analysis of the 2-propyl derivative 3a proved (R)-configuration of the major diastereomer and led to the correction of our earlier assignment of configuration for (-)-coniine hydrochloride 9a obtained from this intermediate. Despite their low reactivity, these enaminones 3 can be converted into chiral 2,6-cis-disubstituted piperidinones 12 with high stereoselectivity by reaction with organocuprates in combination with hard electrophiles. Enantiomerically pure alkaloids such as (-)-dihydropinidine and gephyrotoxine 167B have been synthesized according to this methodology.

A straightforward synthesis of (S)-Anabasine via the catalytic, enantioselective vinylogous mukaiyama-Mannich reaction

The tobacco alkaloid (S)-anabasine was synthesized by a straightforward 4-step sequence with the catalytic enantioselective vinylogous Mannich reaction as a key step. Only 3 mol% of a structurally optimized chiral BINOL-based phosphoric acid was employed to control the absolute configuration of the natural product. Georg Thieme Verlag Stuttgart.

4-[(4'-Methylphenyl)sulfonyl]-1-(trophenylphosphoranylidene)-2-butanone as a New Four-Carbon Synthon for Substituted Divinyl Ketones

The title compound and the corresponding anion have been conveniently used as precursors of substituted divinylketones in both carbo- and heterocyclization reactions in one-pot, three-step sequences leading to a wide variety of substituted carbo- and heterocyclic ring systems, as well as to multifunctionalized linear carbon frameworks. The compounds generated through the use of this multi-coupling reagent represent useful synthons for the construction of natural compounds including (+/-)-epibatidine, (-)-anabasine and (+/-)-pyrenophorin.

Asymmetric aza-Diels-Alder reaction: Enantio- and diastereoselective reaction of imine mediated by Chiral Lewis acid

An efficient asymmetric aza-Diels-Alder reaction using chiral boron mediator is developed. The key to its success is the use of the chiral boron complex prepared in situ from (R)- or (S)- binaphthol and B(OPh)3. The enantiomeric reaction of prochiral imine affords products of up to 90% ee. The double asymmetric induction of chiral imine using α-benzylamine as a chiral auxiliary is achieved with almost complete diastereoselectivity for both aliphatic and aromatic aldimines. This method is applied to the efficient synthesis anabasine and coniine of piperidine alkaloides.