Asymmetric aminocarbonylation of iodoalkenes in the presence of α-phenylethylamine as an N -nucleophile

Mikle, Gábor; Boros, B; Kollár, László

doi:10.1016/j.tetasy.2017.10.012

Cited by 10 publications

(5 citation statements)

References 30 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Based on our preliminary investigations with similar iodoalkene functionalities, i.e., their use in aminocarbonylation/cyclization sequence to obtain oxazoles (Szuroczki et al 2018), as well as in asymmetric aminocarbonylation to obtain diastereoisomers of various carboxamides (Mikle 2017), a systematic investigation regarding the structure of both substrate and N-nucleophile was decided. In the present paper, a facile procedure for the synthesis of 20-carboxamidopregnenes is described using the 20-keto-20-hydrazone-20-iodo-20-ene-20-carboxamido-20-ene reaction pathway.…”

Section: ) Provided a Solidmentioning

confidence: 99%

Synthesis of novel pregnane-based 20-carboxamides via palladium-catalysed aminocarbonylation

et al. 2021

Self Cite

View full text Add to dashboard Cite

Abstract20-Carboxamidopregnene derivatives, such as 3β-acetoxy-5α-pregn-20-ene-20-carboxamides and 5α-pregn-20-ene-20-carboxamides were synthesized from the widely accessible 3β-acetoxy-pregn-5,16-dien-20-one (PDA) using selective hydrogenation, hydrazine and iodoalkene formation, as well as palladium-catalysed aminocarbonylation. The 20-iodo-20-ene derivatives, obtained from the corresponding 20-keto derivatives via their hydrazones, served as substrates. 23 new 20-carboxamides were obtained using various N-nucleophiles ranging from simple primary amines to α-amino acid esters. The novelty of this methodology lies in the application of facile, moderate or high-yielding reactions to obtain otherwise hardly accessible steroidal 20-carboxamides of pharmaceutical importance. In other words, instead of the enzymatic or synthetic degradation of e.g., sterols or cholanic acids, functionalization of the basic skeleton (a ‘building-up’ approach) was used.

show abstract

Section: ) Provided a Solidmentioning

confidence: 99%

Synthesis of novel pregnane-based 20-carboxamides via palladium-catalysed aminocarbonylation

et al. 2021

Self Cite

View full text Add to dashboard Cite

show abstract

“…The palladium-catalyzed aminocarbonylation of alkenyl iodides enjoys interest as an important method for the introduction of new carbonyl functionality in organic compounds. Kollár's group described the stereochemistry of products obtained in the asymmetric aminocarbonylation of iodoalkenes [61]. They presented the reaction of chiral iodoalkenes with α-PEA in the presence of Pd catalyst.…”

Section: Asymmetric Aminocarbonylation Of Iodoalkenesmentioning

confidence: 99%

New Advances in the Synthetic Application of Enantiomeric 1-Phenylethylamine (α-PEA): Privileged Chiral Inducer and Auxiliary

Wosińska-Hrydczuk

Skarżewski

2020

Molecules

View full text Add to dashboard Cite

New developments in the synthesis, resolution, and synthetic applications of chiral 1-phenylethylamine (α-PEA) reported in the last decade have been reviewed. In particular, improvements in the synthesis of α-PEA and its derivatives and chiral resolution, as well as their applications in the resolution of other compounds, were discussed. α-PEA was used as a chiral auxiliary in the diastereoselective synthesis of medicinal substances and natural products. Chiral ligands with α-PEA moieties were applied in asymmetric reactions, and effective modular chiral organocatalysts were constructed with α-PEA fragments and used in important synthetic reactions.

show abstract

“…Since the discovery of the aminocarbonylation by Heck et al (“Heck-carbonylation”) [ 23 , 24 , 25 ], the use of a primary or secondary amine, carbon monoxide, and aryl/alkenyl halides (or their synthetic surrogates, aryl triflates, and alkenyl triflates) in the presence of palladium catalysts leads to carboxamides in great variety [ 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 ]. Several α,β-unsaturated carboxamides and aryl carboxamides, using palladium-catalyzed aminocarbonylation as a key reaction, were recently synthesized in our laboratory [ 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 ]. Just to illustrate the most recent developments, the functionalization of aromatic N -heterocycles in aminocarbonylation should be mentioned [ 46 , 47 , 48 , 49 ].…”

Section: Introductionmentioning

confidence: 99%

Selective Synthesis of N-Acylnortropane Derivatives in Palladium-Catalysed Aminocarbonylation

et al. 2021

Self Cite

View full text Add to dashboard Cite

The aminocarbonylation of various alkenyl and (hetero)aryl iodides was carried out using tropane-based amines of biological importance, such as 8-azabicyclo[3.2.1]octan-3-one (nortropinone) and 3α-hydroxy-8-azabicyclo[3.2.1]octane (nortropine) as N-nucleophile. Using iodoalkenes, the two nucleophiles were selectively converted to the corresponding amide in the presence of Pd(OAc)2/2 PPh3 catalysts. In the presence of several iodo(hetero)arenes, the application of the bidentate Xantphos was necessary to produce the target compounds selectively. The new carboxamides of varied structure, formed in palladium-catalyzed aminocarbonylation reactions, were isolated and fully characterized. In this way, a novel synthetic method has been developed for the producing of N-acylnortropane derivatives of biological importance.

show abstract

Asymmetric aminocarbonylation of iodoalkenes in the presence of α-phenylethylamine as an N -nucleophile

Cited by 10 publications

References 30 publications

Synthesis of novel pregnane-based 20-carboxamides via palladium-catalysed aminocarbonylation

Synthesis of novel pregnane-based 20-carboxamides via palladium-catalysed aminocarbonylation

New Advances in the Synthetic Application of Enantiomeric 1-Phenylethylamine (α-PEA): Privileged Chiral Inducer and Auxiliary

Selective Synthesis of N-Acylnortropane Derivatives in Palladium-Catalysed Aminocarbonylation

Contact Info

Product

Resources

About