A Novel [3+2] Dipolar
Cycloaddition Approach to Hexahydrobenzofuro[3,2-<i>b</i>]pyrroles

Kim, Ikyon; Na, Hee Kyung; Kim, Kyung Ran; Kim, Sun Gi; Lee, Ge Hyeong

doi:10.1055/s-2008-1077951

Cited by 14 publications

(3 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…20 Then, it was expected that the 1,3-dipole (5), generated from 1 with sarcosine, would react with the neighboring double bond to give a structurally novel bicyclo[3.2.1]octane ring system (6b), Scheme 1. 21 However, contrary to anticipation, a linearly fused tricyclic 914 HAMZEHLOUEIAN et al compound 7f was obtained as the major product instead (Scheme 1). In the present work, as a part of an ongoing theoretical and experimental research program on 1,3-dipolar cycloaddition reactions, 22 a theoretical study on the observed difference in regioselectivity of the above reactions was performed, in order to achieve a deeper insight to IMHDA and IMDCA.…”

Section: Introductionmentioning

confidence: 92%

“…These results are in agreement with the experimental findings that for the IMHDA reaction of compound 2, the bridged product 3b is the major product 20 but for the IMDCA reaction of 5, the fused product 7f is favored. 21 In order to calculate the charge transfer and reactivity indices for an intramolecular reaction, it is necessary to consider a molecule as two fragments: diene (D) and dienophile (Dp) for IMHDA and dipole (D) and dipolarophile (Dp) for IMDCA. The embedded fragments in 2 and 5 are shown in Fig.…”

Section: Energies Of Transition State Structuresmentioning

confidence: 99%

See 1 more Smart Citation

A theoretical investigation on the regioselectivity of the intramolecular hetero Diels-Alder and 1,3-dipolar cycloaddition of 2-vinyloxybenzaldehyde derivatives

Hamzehloueian

Yeganegi

Sarrafi

et al. 2014

JSCS

View full text Add to dashboard Cite

The present paper reports a systematic computational analysis study of the two possible pathways, fused and bridged, for an intramolecular hetero Diels-Alder (IMHDA) and an intramolecular 1,3-dipolar cycloaddition (IMDCA) of 2-(vinyloxy)benzaldehyde derivatives. The potential energy surface analyses for both reactions are in agreement with the experimental observations. The activation energies associated with the two regioisomeric channels in the IMHDA reaction showed that the bridged product is favored, although in the IMDCA, the most stable transition state results in the fused product. The global electronic properties of the fragments within each molecule were studied to discuss the reactivity patterns and charge transfer direction in the intramolecular processes. The asynchronicity of the bond formation and aromaticity of the optimized TSs in the Diels-Alder reaction as well as cycloaddition reaction were evaluated. Finally, the 1 H-NMR chemical shifts of the possible regioisomers were calculated using the GIAO method, the values of which for the most stable products were in agreement with the experimental data for both reactions.

show abstract

Section: Introductionmentioning

confidence: 92%

Section: Energies Of Transition State Structuresmentioning

confidence: 99%

A theoretical investigation on the regioselectivity of the intramolecular hetero Diels-Alder and 1,3-dipolar cycloaddition of 2-vinyloxybenzaldehyde derivatives

Hamzehloueian

Yeganegi

Sarrafi

et al. 2014

JSCS

View full text Add to dashboard Cite

show abstract

“…The IMPC regioselectivities of azomethine ylides are inherently attributed to the intramolecular nature of the reactions . An effort to switch the regioselectivity to IMCC failed, and theoretical calculations also indicate that the [3+2]IMPC is much preferred both kinetically and thermodynamically …”

Section: Figurementioning

confidence: 99%

Lewis Acid‐Catalyzed Intramolecular [3+2] Cross‐Cycloaddition of Aziridine 2,2‐Diesters with Conjugated Dienes for Construction of Aza‐[n.2.1] Skeletons

Zhan

Liu

Ren

et al. 2017

Chemistry A European J

View full text Add to dashboard Cite

A novel Lewis acid-catalyzed [3+2] intramolecular cross-cycloaddition (IMCC) between aziridine 2,2-diesters and conjugated dienes has been developed. This is the first regiospecific IMCC of intramolecular 1,3-dipolar cycloadditions of azomethine ylides with carbon=carbon double bonds, and supplies a general and efficient strategy for construction of structurally complex and diverse aza-[n.2.1] skeletons. The [3+2]IMCC could be carried out under mild conditions and in gram scale. More importantly, 3-alkyl-substituted aziridines were also successful. The excellent structural diversity, the facile operation and the versatile post-modifications will support the applications of the [3+2]IMCC in natural products synthesis and drugs discovery.

show abstract

ChemInform Abstract: A Novel [3 + 2] Dipolar Cycloaddition Approach to Hexahydrobenzofuro[3,2‐b]pyrroles.

Kim

et al. 2008

ChemInform

View full text Add to dashboard Cite

Fused pyrrole derivatives R 0160A Novel [3 + 2] Dipolar Cycloaddition Approach to Hexahydrobenzofuro[3,2-b]pyrroles. -The ring system is prepared by stereoselective intramolecular cycloaddition of azomethine ylides, generated from 2-vinyloxybenzaldehydes. The method is also applicable to secondary amino acids providing indolizidines of type (V) under similar conditions. -(KIM*, I.; NA, H.-K.; KIM, K. R.; KIM, S. G.; LEE, G. H.;

show abstract

A Novel [3+2] Dipolar Cycloaddition Approach to Hexahydrobenzofuro[3,2-b]pyrroles

Abstract: A highly stereoselective intramolecular 1,3-dipolar cycloaddition reaction of azomethine ylides derived from 2-vinyloxybenzaldehydes proceeded smoothly to allow for a direct access to tricyclic hexahydrobenzofuro[3,2-b]pyrroles in good yields.

Cited by 14 publications

References 2 publications

A theoretical investigation on the regioselectivity of the intramolecular hetero Diels-Alder and 1,3-dipolar cycloaddition of 2-vinyloxybenzaldehyde derivatives

A theoretical investigation on the regioselectivity of the intramolecular hetero Diels-Alder and 1,3-dipolar cycloaddition of 2-vinyloxybenzaldehyde derivatives

Lewis Acid‐Catalyzed Intramolecular [3+2] Cross‐Cycloaddition of Aziridine 2,2‐Diesters with Conjugated Dienes for Construction of Aza‐[n.2.1] Skeletons

ChemInform Abstract: A Novel [3 + 2] Dipolar Cycloaddition Approach to Hexahydrobenzofuro[3,2‐b]pyrroles.

Contact Info

Product

Resources

About