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Synthetic Exploration of alpha-Diazo gamma-Butyrolactams. / Zhukovsky, Daniil; Dar'in, Dmitry; Kantin, Grigory; Krasavin, Mikhail.

In: European Journal of Organic Chemistry, Vol. 2019, No. 13, 09.04.2019, p. 2397-2400.

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

Harvard

Zhukovsky, D, Dar'in, D, Kantin, G & Krasavin, M 2019, 'Synthetic Exploration of alpha-Diazo gamma-Butyrolactams', European Journal of Organic Chemistry, vol. 2019, no. 13, pp. 2397-2400. https://doi.org/10.1002/ejoc.201900133

APA

Zhukovsky, D., Dar'in, D., Kantin, G., & Krasavin, M. (2019). Synthetic Exploration of alpha-Diazo gamma-Butyrolactams. European Journal of Organic Chemistry, 2019(13), 2397-2400. https://doi.org/10.1002/ejoc.201900133

Vancouver

Zhukovsky D, Dar'in D, Kantin G, Krasavin M. Synthetic Exploration of alpha-Diazo gamma-Butyrolactams. European Journal of Organic Chemistry. 2019 Apr 9;2019(13):2397-2400. https://doi.org/10.1002/ejoc.201900133

Author

Zhukovsky, Daniil ; Dar'in, Dmitry ; Kantin, Grigory ; Krasavin, Mikhail. / Synthetic Exploration of alpha-Diazo gamma-Butyrolactams. In: European Journal of Organic Chemistry. 2019 ; Vol. 2019, No. 13. pp. 2397-2400.

BibTeX

@article{58fe295376ad47bb89d3b19c071003d1,
title = "Synthetic Exploration of alpha-Diazo gamma-Butyrolactams",
abstract = "DIazo transfer reaction onto γ-butyrolactams (activated by α-ethyloxalylation) gave rare α-diazo γ-butyrolactams. Decomposition of the latter by Rh 2 (OAc) 4 in the presence of alcohols and water gave products of O–H insertion of the respective metal-cabene species. Silver triflate (1 mol-%) was found to convert the γ-butyrolactams investigated into 1,5-dihydro-2H-pyrrol-2-ones which represent versatile building blocks. Particular instability was noted for α-diazo γ-butyrolactams bearing alkyl or o-substituted aryl substituents on the nitrogen atom. These were found to dimerize in solution or upon storage at room temperature to give fully conjugated bis-hydrazones along with the loss of a nitrogen molecule. ",
keywords = "1,2-Hydride shift, 3-Pyrrolin-2-ones, Diazo-transfer, O–H insertion, α-Diazolactams, γ-Butyrolactams, ASYMMETRIC-SYNTHESIS, ENANTIOSELECTIVE SYNTHESIS, O-H insertion, STRATEGY, alpha-Diazolactams, INSERTION REACTION, gamma-Butyrolactams, DIAZOKETONES, LACTAMS, SELECTIVITY, METATHESIS, CONJUGATE ADDITION, DIHYDROFURANS",
author = "Daniil Zhukovsky and Dmitry Dar'in and Grigory Kantin and Mikhail Krasavin",
year = "2019",
month = apr,
day = "9",
doi = "10.1002/ejoc.201900133",
language = "English",
volume = "2019",
pages = "2397--2400",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley-Blackwell",
number = "13",

}

RIS

TY - JOUR

T1 - Synthetic Exploration of alpha-Diazo gamma-Butyrolactams

AU - Zhukovsky, Daniil

AU - Dar'in, Dmitry

AU - Kantin, Grigory

AU - Krasavin, Mikhail

PY - 2019/4/9

Y1 - 2019/4/9

N2 - DIazo transfer reaction onto γ-butyrolactams (activated by α-ethyloxalylation) gave rare α-diazo γ-butyrolactams. Decomposition of the latter by Rh 2 (OAc) 4 in the presence of alcohols and water gave products of O–H insertion of the respective metal-cabene species. Silver triflate (1 mol-%) was found to convert the γ-butyrolactams investigated into 1,5-dihydro-2H-pyrrol-2-ones which represent versatile building blocks. Particular instability was noted for α-diazo γ-butyrolactams bearing alkyl or o-substituted aryl substituents on the nitrogen atom. These were found to dimerize in solution or upon storage at room temperature to give fully conjugated bis-hydrazones along with the loss of a nitrogen molecule.

AB - DIazo transfer reaction onto γ-butyrolactams (activated by α-ethyloxalylation) gave rare α-diazo γ-butyrolactams. Decomposition of the latter by Rh 2 (OAc) 4 in the presence of alcohols and water gave products of O–H insertion of the respective metal-cabene species. Silver triflate (1 mol-%) was found to convert the γ-butyrolactams investigated into 1,5-dihydro-2H-pyrrol-2-ones which represent versatile building blocks. Particular instability was noted for α-diazo γ-butyrolactams bearing alkyl or o-substituted aryl substituents on the nitrogen atom. These were found to dimerize in solution or upon storage at room temperature to give fully conjugated bis-hydrazones along with the loss of a nitrogen molecule.

KW - 1,2-Hydride shift

KW - 3-Pyrrolin-2-ones

KW - Diazo-transfer

KW - O–H insertion

KW - α-Diazolactams

KW - γ-Butyrolactams

KW - ASYMMETRIC-SYNTHESIS

KW - ENANTIOSELECTIVE SYNTHESIS

KW - O-H insertion

KW - STRATEGY

KW - alpha-Diazolactams

KW - INSERTION REACTION

KW - gamma-Butyrolactams

KW - DIAZOKETONES

KW - LACTAMS

KW - SELECTIVITY

KW - METATHESIS

KW - CONJUGATE ADDITION

KW - DIHYDROFURANS

UR - http://www.scopus.com/inward/record.url?scp=85064037393&partnerID=8YFLogxK

UR - http://www.mendeley.com/research/synthetic-exploration-%CE%B1diazo-%CE%B3butyrolactams

U2 - 10.1002/ejoc.201900133

DO - 10.1002/ejoc.201900133

M3 - Article

VL - 2019

SP - 2397

EP - 2400

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 13

ER -

ID: 47798372