138371-96-7

Upstream product

• 13735-81-4 1-styrenyloxytrimethylsilane 
• 119910-09-7 N-tert-butoxycarbonyl-2-ethoxypiperidine 
• 195964-51-3 tert-butyl 2-methoxypiperidine-1-carboxylate 
• 85908-96-9 2-oxopiperidine-1-carboxylic acid tert-butyl ester 
• 132205-80-2 dimethyl phosphonate 
• 157634-02-1 tert-butyl 2-formylpiperidine-1-carboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 30800-90-9 1-phenyl-2-(piperidin-2-yl)ethan-1-one 
• 536-74-3 phenylacetylene 
• 91951-58-5 tert-butyl (tetrahydro-2H-pyran-2-yl)carbamate 
• 66324-10-5 tert-butyldimethyl(1-phenylvinyloxy)silane 
• 123387-55-3 1-t-butoxycarbonyl-2-tributylstannylpiperidine 

Downstream Products

• 138371-97-8 (1RS,2SR) N-tert-butoxycarbonyl-2-(β-hydroxy-β-phenylethyl)piperidine 
• 138371-97-8 (1SR,2SR) N-tert-butoxycarbonyl-2-(β-hydroxy-β-phenylethyl)piperidine 
• 30800-90-9 1-phenyl-2-(piperidin-2-yl)ethan-1-one 
• 7773-46-8 2-(1-methylpiperidin-2-yl)-1-phenylethan-1-ol 
• 495-47-6 (±)-norsedamine 
• 497-88-1 sedamine 

Relevant academic research and scientific papers

Oxidative Generation of N-Acyliminium Ions from N-1-(Tributylstannyl)alkyl Carboxamides and Carbamates and Their Reactions with Carbon Nucleophiles

Oxidation of N-1-(tributylstannyl)alkyl carboxamides and carbamates with ammonium hexanitratocerate (IV) or ferrocenium hexafluorophosphate generates their N-acyliminium ions by the elimination of tributylstannyl radical under mild reaction conditions.The

Addition of carbon nucleophiles to cyclic N-acyliminium ions in SDS/water

The acid-catalyzed addition of 1,3-dicarbonyl compounds and activated olefins (silyl enol ethers and ethyl vinyl ether) to N-Boc-2-methoxypyrrolidine (1a) and N-Boc-2-methoxypiperidine (1b) in SDS/water medium is described. Good yields of the correspondin

Gold(I)/(III)-catalyzed synthesis of 2-substituted piperidines; valency-controlled cyclization modes

Strategic use of hard gold(III) and soft gold(I) catalysts provides facile access to two types of 2-substituted piperidines from propargylic alcohols. Thus, heating propargylic alcohols in the presence of AuBr3 results in cyclization to furnish

Synthesis of a 3,4-Dihydro-1,3-oxazin-2-ones Skeleton via an Intermolecular [4 + 2] Process of N-Acyliminium Ions with Ynamides/Terminal Alkynes

An approach to access functionalized 3,4-dihydro-1,3-oxazin-2-ones has been developed by reacting semicyclic N,O-acetals 5 and 6 with ynamides 7 or terminal alkynes 8 in a one-pot fashion. The reaction went through a formal [4 + 2] cycloaddition process to generate a number of functionalized 3,4-dihydro-1,3-oxazin-2-ones 9a-9ak and 10a-10bc in yields of 34-97%. In addition, the utility of this transformation was demonstrated by the synthesis of (±)-sedamine 13.

Pd-catalyzed enantioselective aerobic oxidation of secondary alcohols: Applications to the total synthesis of alkaloids

Enantioselective syntheses of the alkaloids (-)-aurantioclavine, (+)-amurensinine, (-)-lobeline, and (-)- and (+)-sedamine are described. The syntheses demonstrate the effectiveness of the Pd-catalyzed asymmetric oxidation of secondary alcohols in diverse contexts and the ability of this methodology to set the absolute configuration of multiple stereocenters in a single operation. The utility of an aryne C-C insertion reaction in accessing complex polycyclic frameworks is also described.

Addition of carbon nucleophiles to cyclic N-acyliminium and oxocarbenium ions under solvent-free conditions

The InCl3-catalyzed addition of carbon nucleophiles to cyclic N-acyliminium and oxocarbenium ions under solvent-free conditions at room temperature is described. The corresponding α-substituted heterocycles were obtained in moderate to excellen

Addition of activated olefins to cyclic N-acyliminium ions in ionic liquids

Organoindate(III) ionic liquid (BMI?InCl4) was successfully employed in the nucleophilic addition of allyltrimethylsilane, silyl enol ethers and ketene silyl acetals to in situ generated cyclic N-acyliminium ions at room temperature without the

Zinc triflate as Lewis acid in nucleophilic addition to cyclic N-acyliminium ions

Zinc triflate-mediated nucleophilic addition of allytrimethylsilane, silyl enol ethers and terminal acetylenes to cyclic N-acyliminium ions at room temperature in CH2Cl2 is described. The corresponding α-substituted heterocycles were

Trimethylsilyl trifluoromethanesulfonate (TMSOTf) catalyzed amidoalkylation of silylenolethers. Stereocontrolled syntheses of (+/-)-sedamine and (+/-)-norsedamine

Trimethylsilyl trifluoromethanesulfonate (TMSOTf) catalyzed addition of 1-trimethylsilyloxy-1-phenylethene to N-ethoxycarbonyl- and N-tert-butoxycarbonyl-2-ethoxypiperidines (3a and 3b, respectively) afforded the corresponding ketocarbamates 4a and 4b, in excellent yields. Stereoselective conversion to (±)-norsedamine (7) and (±)-sedamine (8) is described.