67008-24-6

Upstream product

• 98712-01-7 (-)-(2R)-N-carbomethoxynorsedaminone 
• 50-00-0 formaldehyd 
• 639458-45-0 2-(2-hydroxy-2-phenyl-ethyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 934472-16-9 2-(2-hydroxy-2-phenyl-ethyl)-piperidine-1-carboxylic acid benzyl ester 
• 112653-26-6 (1S)-1-Phenyl-2<(2R)-2-piperidyl>ethanol 
• 757956-02-8 methoxymethyl-[(1S)-2-((R)-oxiranyl)-1-phenylethyl] ether 
• 118811-03-3 tert-butyl 2-(2-hydroxyethyl)piperidine-1-carboxylate 
• 639458-46-1 (R)-2-(2-oxo-ethyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 639458-48-3 (R)-2-(2-acetoxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 639458-47-2 (R)-2-((S)-2-hydroxy-2-phenylethyl)-piperidine-1-carboxylic acidtert-butyl ester 
• 101113-68-2 (+/-)-sedaminone 
• 134040-02-1 (R)-2-((R)-2-Hydroxy-2-phenyl-ethyl)-piperidine-1-carboxylic acid methyl ester 
• 138371-93-4 (1SR,2SR) N-ethoxycarbonyl-2-(β-hydroxy-β-phenylethyl)piperidine 
• 70546-72-4 (2S,3aR)-8-Methyl-2-phenyl-hexahydro-isoxazolo[2,3-a]pyridin-8-ium; iodide 

Downstream Products

• 221022-81-7 2-((R)-1-methyl-[2]piperidyl)-1-phenyl-ethanone 
• 70561-76-1 (±)-allosedamine 
• 67008-23-5 (2R)-2-((2R)-2-hydroxy-2-phenylethyl)-1-methylpiperidine 
• 497-88-1 (-)-sedamine 

Relevant academic research and scientific papers

Decarboxylative Conjunctive Cross-coupling of Vinyl Boronic Esters using Metallaphotoredox Catalysis

The synthesis of complex alkyl boronic esters through conjunctive cross-coupling of vinyl boronic esters with carboxylic acids and aryl iodides is described. The reaction proceeds under mild metallaphotoredox conditions and involves an unprecedented decarboxylative radical addition/cross-coupling cascade of vinyl boronic esters. Excellent functional-group tolerance is displayed, and application of a range of carboxylic acids, including secondary α-amino acids, and aryl iodides provides efficient access to highly functionalized alkyl boronic esters. The decarboxylative conjunctive cross-coupling was also applied to the synthesis of sedum alkaloids.

Stereoselective asymmetric synthesis of (+)-sedamine and (+)-allosedamine

A convenient method for the generation of (+)-sedamine and (+)-allosedamine in high optical purity has been elaborated. The key steps are the highly stereoselective 1,2-nucleophilic addition to SAMP hydrazones allowing the installation of the stereogenic center at C2 and ring closing metathesis.

A rapid access to (±)-sedamine and some original N -benzyl unsaturated analogues

Reduction of N-alkyl-2-(2-hydroxy-2-phenylethyl)pyridinium salts using excess of sodium triacetoxyborohydride afforded exclusively the corresponding tetrahydropyridine derivative bearing a piperidine ring with a double bond in the 3,4-position. Furthermore, under these conditions, syn-1,3-amino alcohols were obtained in good yield and diastereoselectivity. Georg Thieme Verlag Stuttgart · New York.

Asymmetric synthesis of Sedum alkaloids via lithium amide conjugate addition

Conjugate addition of lithium (R)-N-allyl-N-(α-methylbenzyl)amide or lithium (R)-N-but-3-enyl-N-(α-methylbenzyl)amide to an alkyl hexa-2,4-dienoate or alkyl hepta-2,6-dienoate, followed by ring-closing metathesis of the olefin functionalities within the resultant β-amino ester, generates a range of diastereoisomerically pure azacycles in good yield. These homochiral templates are readily transformed to a range of piperidine alkaloids of the Sedum family, and the corresponding five-, seven- and eight-membered ring homologues.

Hydroformylation of homoallylic azides: A rapid approach toward alkaloids

(Chemical Equation Presented) Unprecedented hydroformylation of homoallylic azides combined with useful one-pot operations provides an expeditive access to alkaloids.

An efficient approach to 2-substituted N-tosylpiperdines: asymmetric synthesis of 2-(2-hydroxy substituted)piperidine alkaloids

We have developed an efficient and a general approach to chiral 2-substituted N-tosylpiperidines starting from chiral α-substituted-N-tosylaziridines. Using this approach, we have synthesized (+)-coniine. The synthesis of chiral N-tosyl-2-piperidinylethanol 15 and ent-15, was achieved from l- and d-aspartic acids, respectively in few steps. Piperidine 15 was converted into 2-(2-hydroxysubstituted)piperidines of type 2 in optically active form. By applying this strategy, asymmetric syntheses of halosaline (R,R)-2a, (+)- and (-)-sedamine 2b, (+)- and (-)-allosedamine 2c, (+)- and (-)-sedridine 2d, (+)- and (-)-allosedridine 2e, (+)-tetraponerine T-3 3a, T-4 3c, T-7 3b, and T-8 3d have been achieved in high yields. These stereoisomers can be interconverted via Mitsunobu inversion in excellent yields.

Enantioselective organocatalytic intramolecular aza-Michael reaction: A concise synthesis of (+)-sedamine, (+)-allosedamine, and (+)-coniine

(Chemical Equation Presented) The intramolecular aza-Michael reaction of carbamates bearing remote α,β-unsaturated aldehydes under organocatalytic conditions took place with good yields and excellent ee's when Jorgensen catalyst IV was used in the process, giving rise to the enantioselective formation of several five- and six-membered heterocycles. The developed methodology was applied to the synthesis of three piperidine alkaloids.

Enantioselective synthesis of lobeline via nonenzymatic desymmetrization

Lobeline has been prepared in enantiopure form via desymmetrization of lobelanidine with use of BTM, a nonenzymatic enantioselective acyl transfer catalyst.

A facile synthetic route to (+)-allosedamine via hydrolytic kinetic resolution and olefin metathesis

A concise synthesis of (+)-allosedamine has been achieved using cobalt-catalyzed hydrolytic kinetic resolution (HKR) and ruthenium-catalyzed ring closing metathesis (RCM) as two key steps, in which HKR was used to introduce both stereogenic centers in the natural compound with a high degree of diastereomeric ratio and cyclization was carried out with the well developed RCM procedure.

Remote Stereocenter Discrimination in the Enzymatic Resolution of Piperidine-2-ethanol. Short Enantioselective Synthesis of Sedamine and Allosedamine

Kinetic resolution of N-Boc-piperidine-2-ethanol (2), a case of remote stereocenter discrimination, was accomplished by sequential transesterification mediated by two enzymes, Lipase PS and porcine pancreatic lipase, showing opposite enantioselectivity. The gram-scale availability of the two enantiomeric N-Boc alcohols 2a (R) and 2c (S) enlarges their synthetic exploitation for the enantioselective preparation of piperidine alkaloids. As an example, the convenient three-step synthesis of both the enantiomers of sedamine and allosedamine is described.