Preparation of N-alkyl pyrrolidinones via photocyclization of γ-keto-α,β-unsaturated amides

Dittami, James P.; Xu, Feng; Hua, Qi; Martin, Matthew W.; Bordner, Jon; Decosta, D. L.; Kiplinger, Jeffrey P.; Reiche, P.; Ware, R.

doi:10.1016/0040-4039(95)00779-c

Cited by 16 publications

(5 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…[132] Eine weitere Variante der Norrish-Yang-Cyclisierung aus neuerer Zeit wurde von Wessig und Teubner zur Synthese von (AE )-Pterosin B (88) und C genutzt (Schema 25). [133] Dabei wurde ausgehend von Keton 84 durch eine Spinzentrenverschiebung [134] Analog zur klassischen Norrish-Yang-Cyclisierung können auch a,b-ungesättigte g-Ketoamide zu N-Alkylpyrrolidinonen umgesetzt werden, [136] was in einer Totalsynthese von (AE )-Jatropham angewendet wurde. [137] 4.…”

Section: Aufsätzeunclassified

Photochemische Reaktionen als Schlüsselschritte in der Naturstoffsynthese

2011

View full text Add to dashboard Cite

Photochemische Reaktionen bereichern in signifikanter Weise das Repertoire zur Knüpfung von Kohlenstoff‐Kohlenstoff‐Bindungen und machen ungewöhnliche, auf herkömmlichem Weg nicht erhältliche Molekülgerüste zugänglich. In diesem Aufsatz werden die wichtigsten Umsetzungen der Photochemie vorgestellt, die auf breiter Front Einzug in die Naturstoffsynthese gehalten haben. Beispielhaft werden einzelne Totalsynthesen diskutiert, wobei besonderes Augenmerk auf den photochemischen Schlüsselschritt sowie dessen Stereoselektivität gerichtet ist. Dabei wird das photochemisch erzeugte Molekül in Relation zur Struktur des Naturstoffs gebracht, und Folgereaktionen werden, wo notwendig, illustriert und klassifiziert.

show abstract

Section: Aufsätzeunclassified

Photochemische Reaktionen als Schlüsselschritte in der Naturstoffsynthese

2011

View full text Add to dashboard Cite

show abstract

“…We designed a reaction involving efficient photoisomerization followed by reversible cyclization, as shown in Scheme , leading to an aminal structure as in isoindolinones. The prochiral aroylacrylamide 1 has an enone structure; thus, effective isomerization of the alkenyl group from E to Z was expected . Furthermore, it was anticipated that intramolecular hydrogen bonding between the NH and carbonyl groups would stabilize the Z form.…”

Section: Resultsmentioning

confidence: 99%

Asymmetric Synthesis by Using Natural Sunlight under Absolute Achiral Conditions

Sakamoto

Shiratsuki

Uemura

et al. 2017

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…This heterocycle constitute one of the subunits that form the structure of urobilinoid natural pigments. Synthetic 1,5‐dihydropyrrolones and their benzofused analogues (isoindolones) are also of interest in Medicinal Chemistry and in pigment industry . Their preparation has relied on Intramolecular Wittig reactions starting from α‐acylaminoketones 33a.…”

Section: Discussionmentioning

confidence: 99%

Computational studies on the formation of aza‐oxypentadienyl intermediates from alkylidene oxaziridines and keteneimine oxides and their conversion to 1,5‐dihydropyrrolones

Villar

Guillade

González‐Pérez

2018

Int J of Quantum Chemistry

View full text Add to dashboard Cite

The rearrangements of alkylidene oxaziridines 1a,b (a, R = Me; b, R = OMe) and keteneimine oxides 1’a,b to 1,5‐dihydropyrrolones 3a,b have been computationally studied at the UM062X/Def2TZVPP(PCM,TFE)//UM062X/Def2SVP(PCM,TFE) level. The mechanism for conversion of 1a‐3a is predicted to be stepwise, with intermediacy of the acyclic aza‐oxypentadienyl species 4a. The stabilization provided by the nitrogen of the oxaziridine makes the ring opening of 1a to diradical/zwitterionic intermediates 4a more feasible than in the case of the vinyl allene oxide counterparts. The formation of aziridinone 2a from 1a showed competing activation energies but 2a was found to be a thermodynamically less stable species than 3a. When the Me group at N is exchanged by the electron‐donating OMe substituent in 1b, the diradical species and the corresponding transition structures are more stabilized and therefore the aziridinones are not required as intermediates in the conversion of 1b to 3b. Keteneimine oxide 1′ is predicted to directly generate diradical 4 by C‐O ring opening although through a less favored transition state.

show abstract

Preparation of N-alkyl pyrrolidinones via photocyclization of γ-keto-α,β-unsaturated amides

Cited by 16 publications

References 16 publications

Photochemische Reaktionen als Schlüsselschritte in der Naturstoffsynthese

Photochemische Reaktionen als Schlüsselschritte in der Naturstoffsynthese

Asymmetric Synthesis by Using Natural Sunlight under Absolute Achiral Conditions

Computational studies on the formation of aza‐oxypentadienyl intermediates from alkylidene oxaziridines and keteneimine oxides and their conversion to 1,5‐dihydropyrrolones

Contact Info

Product

Resources

About