Synthesis of Protected (1-Phenyl-1<i>H</i>-pyrrol-2-yl)-alkane-1-amines from Phenylnitroso Diels–Alder Adducts with 1,2-Dihydropyridines

Berti, Francesco; Bussolo, Valeria Di; Pineschi, Mauro

doi:10.1021/jo4009996

Cited by 17 publications

(12 citation statements)

References 28 publications

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“…An interesting example is the Diels–Alder reaction with nitrosobenzene, which provides an unusual bicycle that can be opened with CuCl to afford the chiral pyrrole derivative 13 . 26 …”

Section: Resultsmentioning

confidence: 99%

Nickel-catalyzed enantioselective arylation of pyridine

2016

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We report an enantioselective Ni-catalyzed cross coupling of arylzinc reagents with pyridiniumions formed in situ from pyridine and a chloroformate. This reaction provides enantioenriched 2-aryl-1,2-dihydropyridine products that can be elaborated to numerous piperidine derivatives with little or no loss in ee. This method is notable for its use of pyridine, a feedstock chemical, to build a versatile, chiral heterocycle in a single synthetic step.

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“…An interesting example is the Diels–Alder reaction with nitrosobenzene, which provides an unusual bicycle that can be opened with CuCl to afford the chiral pyrrole derivative 13 . 26 …”

Section: Resultsmentioning

confidence: 99%

Nickel-catalyzed enantioselective arylation of pyridine

2016

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“…A direct cleavage of the N−O bond without a preventive elaboration of the double bond was reported by Pineschi and co-workers using titanium(III) salts [35]. In particular, exposing the adduct 4b to TiCl 3 gave rise to a mixture of gem-amino-ether and gem-amino-alcohol derivatives 14a and 14b, respectively, in which the relative stereochemistry of hydroxyl moiety is lost (Scheme 7).…”

Section: Scheme 6 Synthesis Of Iminosugar Derivatives By Streithmentioning

confidence: 77%

Nitroso Diels-Alder Cycloadducts Derived From N-Acyl-1,2-dihydropyridines as a New Platform to Molecular Diversity

2020

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This review focuses upon the use of nitroso Diels–Alder reactions as a structural complexity generating reaction that has been so far a quite scarcely treated topic, despite its potential. In particular, the use of N-acyl-1,2-dihydropyridines as a non-symmetrical diene component in nitroso Diels–Alder reactions encompasses an initial diversification of pathways giving rise to different cycloadducts (direct and inverse). Selective elaborations of these cycloadducts, basically using a reagent-based approach, deliver a discrete number of structurally diverse compounds, including some original heterobicyclic scaffolds and functionalized heterocycles. This forward synthetic planning allowed the individuation of a new biologically active compound based on a novel oxadiaza-bicyclic-[3.3.1]-nonene scaffold which is still under preclinical evaluation.

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“…Subsequently, Pineschi reported the synthesis of pyrroles through the reductive cleavage of phenylnitroso Diels-Alder adducts with 1,2-dihydropyridines, catalyzed by CuCl (Scheme 7). 12 This reaction was carried out in an one-pot procedure without the isolation of nitrosobenzene cycloadduct. The N-O bond of the cycloadduct was reduced to form a tetrahydropyridine which was a cyclic N-acetylated hemiaminal.…”

Section: Cu-catalyzed Synthesis Of Pyrroles From Alkene Derivativesmentioning

confidence: 99%

Recent developments in the group-1B-metal-catalyzed synthesis of pyrroles

et al. 2016

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Pyrroles are important synthetic targets as a result of their occurrence in numerous biologically active molecules, their important roles in diverse living processes, and their utility as versatile intermediates. As a consequence, numerous efforts focused on the development of concise and efficient methods for the construction of pyrroles. Compared with other transition metals, the group 1B metals (Cu, Ag and Au) are probably more versatile and widely used for the synthesis of pyrroles in organic chemistry. Considering the importance of both topics in organic synthesis, here we summarize recent achievements in the synthesis of pyrroles catalyzed by monometallic systems which belong to the group 1B metals (Cu, Ag and Au).

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Synthesis of Protected (1-Phenyl-1H-pyrrol-2-yl)-alkane-1-amines from Phenylnitroso Diels–Alder Adducts with 1,2-Dihydropyridines

Cited by 17 publications

References 28 publications

Nickel-catalyzed enantioselective arylation of pyridine

Nickel-catalyzed enantioselective arylation of pyridine

Nitroso Diels-Alder Cycloadducts Derived From N-Acyl-1,2-dihydropyridines as a New Platform to Molecular Diversity

Recent developments in the group-1B-metal-catalyzed synthesis of pyrroles

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