69261-54-7

Upstream product

• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 14468-80-5 N-benzyloxycarbonylpyrrolidin-2-one 
• 1148-11-4 N-carbobenzyloxyproline 
• 17996-13-3 benzyl 4-hydroxybutylcarbamate 
• 86954-05-4 (S)-2-hydroxymethyl-1-pyrrolidine carboxylic acid phenylmethyl ester 
• 762-72-1 allyl-trimethyl-silane 
• 67-56-1 methanol 
• 172876-96-9 3-oxo-1λ³-benzo[d][1,2]iodaoxole-1(3H)-carbonitrile 
• 1346132-49-7 C₂₈H₃₅NO₃Si 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 5532-86-5 benzyl cyanoformate 
• 501-53-1 benzyl chloroformate 
• 98782-97-9 1-benzyl 2-(4-nitrobenzyl) pyrrolidine-1,2-dicarboxylate 
• 78816-93-0 1-benzyl 2-(2,5-dioxopyrrolidin-1-yl) pyrrolidine-1,2-dicarboxylate 

Downstream Products

• 110910-92-4 N-benzyloxycarbonyl-2-(2-oxopropyl)pyrrolidine 
• 88001-42-7 benzyl 2-methoxypyrrolidine-1-carboxylate 
• 68471-57-8 2,3-dihydro-pyrrole-1-carboxylic acid benzyl ester 
• 96096-65-0 N-[2-(5-methoxy-1H-indol-3-yl)ethyl]benzyloxycarboxamide 
• 476447-08-2 N¹,N⁵,N¹⁰-tri-tert-butoxycarbonyl-N¹⁹-benzyloxycarbonyl-1,5,10,14,19-pentaazanonadecane 
• 153749-83-8 2-(2-oxo-2-phenyl-ethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 174875-26-4 2-(2-oxo-pentyl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 174875-59-3 2-(2-oxo-2-phenyl-ethyl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 880461-84-7 2-(1-methoxycarbonyl-2-oxo-propyl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 676132-43-7 α-allyl-N-benzyloxycarbonylpyrrolidine 
• 1215178-30-5 2-(2-oxobut-3-ynyl)-N-(benzyloxycarbonyl)pyrrolidine 
• 1230072-98-6 benzyl (2S)-2-[2-oxopropyl]pyrrolidine-1-carboxylate 
• 1346132-33-9 benzyl-(2R)-2-(2’-oxopropyl) pyrrolidine-1-carboxylate 
• 1446422-46-3 (R)-dimethyl N-(benzyloxycarbonyl)pyrrolidine-2-phosphonate 

Relevant academic research and scientific papers

One-Pot Double-Annulation Strategy for the Synthesis of Unusual Fused Bis-Heterocycles

A novel metal-free double-annulation cascade for the construction of unusual fused heterocyclic systems is described. This simple protocol enables the sequential assembly of two rings in one pot from two simple precursors. Acidic conditions promote the condensation and the intramolecular alkynyl Prins reaction of an enyne or arenyne alcohol with a cyclic hemiaminal to form a five-, six-, or seven-membered oxacycle followed by a seven-or eight-membered azacycle. In this transformation, chemical complexity is rapidly generated with the formation of three new bonds (one C-O, one C-C, and one C-N) in one synthetic operation. The strategy is modular and relatively general, providing access to a series of unique fused bicyclic scaffolds.

Decarboxylative alkynylation and cyanation of carboxylic acids using photoredox catalysis and hypervalent iodine reagents

Alkynes and nitriles are important functional groups that serve as versatile building blocks in organic synthesis and find applications in material and medicinal sciences. A convenient and straightforward access to both classes of compounds under mild conditions is, therefore, highly desirable. Herein, we disclose the decarb-oxylative alkynylation and cyanation of broadly available carboxylic acids using photoredox catalysis and hyper-valent iodine reagents. Choices of both catalysts and reagents were crucial. Computational and experimental studies revealed two different possible mechanisms that are dictated by the oxidation potential of the reagents: radical for alkynylation, ionic for cyanation.

Microwave versus Conventional Light Activation of O-Radical Scission Processes

Domino or sequential processes initiated by cleavage of O radicals has led to the conversion of low-cost, readily available substrates into high-profit products. The optimization of these processes by using different activation sources (irradiation with v

Enzymatic and chromatographic resolution procedures applied to the synthesis of the phosphoproline enantiomers

The preparation of enantiomerically pure pyrrolidine-2-phosphonic acid (phosphoproline, ProP) has been addressed through the synthesis of suitable racemates and subsequent resolution by independent enzyme-catalyzed and chiral HPLC methods. First, racemic phosphoproline derivatives bearing the necessary protecting groups have been synthesized in excellent global yields starting from inexpensive materials. Preparative HPLC resolution of the N-Cbz-protected aminophosphonate on a cellulose-based column allowed the isolation of enantiomerically pure enantiomers on a gram scale. Enzyme-catalyzed alkoxycarbonylation of the aminophosphonate was studied using different lipases, solvents, and carbonates. Candida antarctica lipase type A (CAL-A) provided the highest enantioselectivity when combined with benzyl 3-methoxyphenyl carbonate.

A dual arylboronic acid-aminothiourea catalytic system for the asymmetric intramolecular hetero-michael reaction of α,β-unsaturated carboxylic acids

A bifunctional aminoboronic acid has been used to facilitate for the first time the intramolecular aza- and oxa-Michael reactions of α,β- unsaturated carboxylic acids. The combination of an arylboronic acid with a chiral aminothiourea allowed for these re

Synthesis and biological activity of potent HIV-1 protease inhibitors based on Phe-Pro dihydroxyethylene isosteres

Peptidomimetic inhibitors of HIV-1 PR are still a key resource in the fight against AIDS. Here we describe the synthesis and biological activity of HIV-1 PR inhibitors based on four novel dihydroxyethylene isosteres of the Phe-Pro and Pro-Pro dipeptides. The isosteres, containing four stereogenic centers, were synthesized in high yield and excellent stereoselectivity via the cyclization of epoxy amines derived from α-amino acids. The inhibitors were assembled by coupling the isosteres with suitable flanking groups and were screened against recombinant HIV PR showing activities in the subnanomolar to micromolar range. Two Phe-Pro-based inhibitors active at the nanomolar level were further investigated: both inhibitors combine the ability to suppress HIV-1 replication in infected MT-2 cells with low cytotoxicity against the same cells, thereby displaying a high therapeutic index. These results demonstrate the potential of the new Phe-Pro dihydroxyethylene isostere as a core unit of powerful HIV-1 PR inhibitors.

Asymmetric organocatalytic intramolecular aza-michael addition of enone carbamates: Catalytic enantioselective access to functionalized 2-substituted piperidines

The synthetically useful functionalized 2-substituted piperidines containing a lateral ketone group have been strategically accessed via an organocatalytic enantioselective intramolecular aza-Michael addition of enone carbamates, in which a novel internal substrate combination of the enone moiety as Michael acceptor and the carbamate moiety as Michael donor was revealed in asymmetric bifunctional organocatalysis. This heteroatom conjugate addition, which was realized by using a catalytic chiral Cinchona-based primary-tertiary diamine and an achiral Bronsted acid, mostly proceeded in high yield and good to excellent stereocontrol (up to 99% ee). This reaction provides an alternative catalytic asymmetric method for installing the stereogenic nitrogen-containing carbon center in functionalized 2-substituted piperidines, leading to the development of a straightforward and expeditious synthesis of some naturally occurring bioactive 2-substituted piperidine alkaloids. Copyright

Hydrozirconation of four-, five-, six- and seven-membered N-alkoxycarbonyl lactams to lactamols

A general, practical, and efficient reduction of four-, five-, six- and, seven-membered N-alkoxycarbonyl lactams to the aldehyde oxidation state is reported. The reduction methodology involves the hydrozirconation reaction by Cp2Zr(H)Cl under m

Potent non-nitrile dipeptidic dipeptidyl peptidase IV inhibitors

The synthesis and structure-activity relationships of novel dipeptidyl peptidase IV inhibitors replacing the classical cyanopyrrolidine P1 group with other small nitrogen heterocycles are described. A unique potency enhancement was achieved with β-branched natural and unnatural amino acids, particularly adamantylglycines, linked to a (2S,3R)-2,3-methanopyrrolidine based scaffold.

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.