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Fused vs. spiro : Kinetic, not thermodynamic preference may direct the reaction of alpha-carbonyl oxonium ylides. / Guranova, Natalia I.; Dar'in, Dmitry; Kantin, Grigory; Novikov, Alexander S.; Bakulina, Olga; Krasavin, Mikhail.

In: Tetrahedron Letters, Vol. 60, No. 24, 13.06.2019, p. 1582-1586.

Research output: Contribution to journal › Article › peer-review

Harvard

Guranova, NI, Dar'in, D, Kantin, G, Novikov, AS, Bakulina, O & Krasavin, M 2019, 'Fused vs. spiro: Kinetic, not thermodynamic preference may direct the reaction of alpha-carbonyl oxonium ylides', Tetrahedron Letters, vol. 60, no. 24, pp. 1582-1586. https://doi.org/10.1016/j.tetlet.2019.05.020

APA

Guranova, N. I., Dar'in, D., Kantin, G., Novikov, A. S., Bakulina, O., & Krasavin, M. (2019). Fused vs. spiro: Kinetic, not thermodynamic preference may direct the reaction of alpha-carbonyl oxonium ylides. Tetrahedron Letters, 60(24), 1582-1586. https://doi.org/10.1016/j.tetlet.2019.05.020

Vancouver

Guranova NI, Dar'in D, Kantin G, Novikov AS, Bakulina O, Krasavin M. Fused vs. spiro: Kinetic, not thermodynamic preference may direct the reaction of alpha-carbonyl oxonium ylides. Tetrahedron Letters. 2019 Jun 13;60(24):1582-1586. https://doi.org/10.1016/j.tetlet.2019.05.020

Author

Guranova, Natalia I. ; Dar'in, Dmitry ; Kantin, Grigory ; Novikov, Alexander S. ; Bakulina, Olga ; Krasavin, Mikhail. / Fused vs. spiro : Kinetic, not thermodynamic preference may direct the reaction of alpha-carbonyl oxonium ylides. In: Tetrahedron Letters. 2019 ; Vol. 60, No. 24. pp. 1582-1586.

BibTeX

@article{710c4dc628ef42c0a2532498f95a7e67,
title = "Fused vs. spiro: Kinetic, not thermodynamic preference may direct the reaction of alpha-carbonyl oxonium ylides",
abstract = "Rh(II)-catalyzed decomposition of certain cyclic α-diazocarbonyl compounds in the presence of cyclic ethers has been shown to give bicyclic ring expansion products. These are thought to arise from a [1,4]-alkyl shift toward the carbonyl oxygen atom and are in contrast with the recently observed spirocyclic products of a Stevens-type [1,2]-alkyl shift within the postulated oxonium ylide intermediate. Quantum chemical calculations performed at the B3LYP/6-31G* level of theory showed that the former reaction pathway (toward fused bicycles) is kinetically preferred.",
keywords = "Kinetic control, Metal carbene species, Oxonium ylides, Quantum chemical calculations, Stevens rearrangement, [1,4]-Alkyl shift, α-Diazocarbonyl compounds, alpha-Diazocarbonyl compounds, CATALYSIS, INSERTION, RING EXPANSION, DECOMPOSITION, REARRANGEMENTS, OXETANES, HETEROCYCLES, CARBENES, DERIVATIVES, MACROCYCLIZATION",
author = "Guranova, {Natalia I.} and Dmitry Dar'in and Grigory Kantin and Novikov, {Alexander S.} and Olga Bakulina and Mikhail Krasavin",
year = "2019",
month = jun,
day = "13",
doi = "10.1016/j.tetlet.2019.05.020",
language = "English",
volume = "60",
pages = "1582--1586",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier",
number = "24",

}

RIS

TY - JOUR

T1 - Fused vs. spiro

T2 - Kinetic, not thermodynamic preference may direct the reaction of alpha-carbonyl oxonium ylides

AU - Guranova, Natalia I.

AU - Dar'in, Dmitry

AU - Kantin, Grigory

AU - Novikov, Alexander S.

AU - Bakulina, Olga

AU - Krasavin, Mikhail

PY - 2019/6/13

Y1 - 2019/6/13

N2 - Rh(II)-catalyzed decomposition of certain cyclic α-diazocarbonyl compounds in the presence of cyclic ethers has been shown to give bicyclic ring expansion products. These are thought to arise from a [1,4]-alkyl shift toward the carbonyl oxygen atom and are in contrast with the recently observed spirocyclic products of a Stevens-type [1,2]-alkyl shift within the postulated oxonium ylide intermediate. Quantum chemical calculations performed at the B3LYP/6-31G* level of theory showed that the former reaction pathway (toward fused bicycles) is kinetically preferred.

AB - Rh(II)-catalyzed decomposition of certain cyclic α-diazocarbonyl compounds in the presence of cyclic ethers has been shown to give bicyclic ring expansion products. These are thought to arise from a [1,4]-alkyl shift toward the carbonyl oxygen atom and are in contrast with the recently observed spirocyclic products of a Stevens-type [1,2]-alkyl shift within the postulated oxonium ylide intermediate. Quantum chemical calculations performed at the B3LYP/6-31G* level of theory showed that the former reaction pathway (toward fused bicycles) is kinetically preferred.

KW - Kinetic control

KW - Metal carbene species

KW - Oxonium ylides

KW - Quantum chemical calculations

KW - Stevens rearrangement

KW - [1,4]-Alkyl shift

KW - α-Diazocarbonyl compounds

KW - alpha-Diazocarbonyl compounds

KW - CATALYSIS

KW - INSERTION

KW - RING EXPANSION

KW - DECOMPOSITION

KW - REARRANGEMENTS

KW - OXETANES

KW - HETEROCYCLES

KW - CARBENES

KW - DERIVATIVES

KW - MACROCYCLIZATION

UR - http://www.scopus.com/inward/record.url?scp=85065525218&partnerID=8YFLogxK

UR - http://www.mendeley.com/research/fused-vs-spiro-kinetic-not-thermodynamic-preference-direct-reaction-%CE%B1carbonyl-oxonium-ylides

U2 - 10.1016/j.tetlet.2019.05.020

DO - 10.1016/j.tetlet.2019.05.020

M3 - Article

AN - SCOPUS:85065525218

VL - 60

SP - 1582

EP - 1586

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 24

ER -

ID: 41855948