96133-48-1

Upstream product

• 69001-12-3 rac-(2-methoxypyrrolidin-1-yl)(phenyl)methanone 
• 5874-58-8 N-(benzoyl)-L-proline 
• 195719-48-3 N-benzoylproline 
• 72351-42-9 [2-(hydroxymethyl)-1-pyrrolidinyl](phenyl)methanone 
• 762-72-1 allyl-trimethyl-silane 
• 512-56-1 trimethyl phosphite 
• 98-88-4 benzoyl chloride 
• 22821-76-7 4-(methylsulfonyl)benzonitrile 
• 3389-54-6 n-benzoylpyrrolidine 

Relevant academic research and scientific papers

Tandem oxidative radical decarboxylation-β-iodination of amino acids. Application to the synthesis of chiral 2,3-disubstituted pyrrolidines

A mild and efficient procedure for the tandem decarboxylation- halogenation of α-amino acids is reported. The iodine is introduced at previously unfunctionalized positions, in good yields. The methodology has been used for the diastereoselective synthesis of 2,3-disubstituted pyrrolidines. (C) 2000 Elsevier Science Ltd.

One-pot synthesis of α-amino phosphonates from α-amino acids and β-amino alcohols

The one-pot radical fragmentation-phosphorylation reaction of α-amino acids and β-amino alcohols affords α-amino phosphonates in good yields. The reaction was applied to the synthesis of potentially bioactive phosphonates.

Decarboxylative Cyanation of Aliphatic Carboxylic Acids via Visible-Light Flavin Photocatalysis

An operationally simple method is disclosed for the decarboxylative cyanation of aliphatic carboxylic acids at room temperature. Riboflavin tetraacetate, which is an inexpensive organic photocatalyst, promotes the oxidation of carboxylic acids upon visible-light activation. After decarboxylation, the generated radicals are trapped by TsCN, yielding the desired nitriles without any further additive, in a redox-neutral process. Importantly, this protocol can be adapted to flow conditions.

Synthesis of alkaloid analogues from β-amino alcohols by β-fragmentation of primary alkoxyl radicals

The fragmentation of primary alkoxyl radicals is usually a minor process with respect to hydrogen abstraction and other competing reactions. However, when β-amino alcohols were used as substrates, the scission proceeded in good to excellent yields and no side reactions were observed. The fragmentation can be coupled with an allylation or alkylation reaction, to give alkaloid analogues and functionalized nitrogen heterocycles. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Synthesis of alkaloids from aminol derivatives by β-fragmentation of primary alkoxyl radicals

The fragmentation of primary alkoxyl radicals, often described as low yielding and plagued by side reactions, proceeded in good to excellent yields when aminol derivatives were used as substrates. Remarkably, no side reactions such as hydrogen abstraction

Chemical conversion of cyclic α-amino acids to cyclic α-aminophosphonic acids

The oxidative decarboxylation of cyclic α-amino acids having urethane-type N-protecting groups with lead tetraacetate [Pb(OAc)4] gave 2-hydroxy derivatives, which were transformed into the corresponding α-aminophosphonic acid esters by treatment of trialkyl phosphites in the presence of Lewis acids. Deprotection and ester cleavage of the products in the usual manner afforded cyclic α-aminophosphonic acids. The convenient chemical conversion of five- and six-membered cyclic α-amino acids to the corresponding cyclic α-aminophosphonic acids has been accomplished.

Synthesis of 2,3-disubstituted pyrrolidines and piperidines via one-pot oxidative decarboxylation-β-iodination of amino acids

A new synthesis of 2,3-disubstituted pyrrolidines and piperidines is described. This mild procedure is based on the one-pot oxidative decarboxylation-β -iodination of α-amino acid carbamates or amides. The iodine is introduced at the previously unfunction

Oxidative decarboxylation of α-amino acids: A mild and efficient method for the generation of N-acyliminium ions

The oxidative decarboxylation of α-amino acids using the system (diacetoxyiodo)benzene or iodosylbenzene and iodine proceeded smoothly at room temperature. The intermediacy of an N-acyliminium cation has been demonstrated through intermolecular and intram

Electroorganic Chemistry. Part 80. α-Hydroxylation of N-Acylated Cyclic Amines and Utilization of the Products as Amino Aldehyde Equivalents

A general method for the transformation of N-acylated cyclic amines (1) to amino aldehydes (4) was exploited.N-Benzoyl- or N-alkoxycarbonyl-α-methoxyamines (2) were prepared by anodic reaction of (1) in methanol.Treatment of (2) with dilute hydrochloric acid gave the corresponding α-hydroxylated compounds (3) which are amino aldehydes equivalents.The reaction of (3) with methoxycarbonylmethylenetriphenylphosphorane yielded ω-amino-α,β-unsaturated esters in satisfactory yields.