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Catalyst-Free Synthesis of Diastereomerically Pure 3-Sulfonyl azetidin-2-ones via Microwave-Assisted Tandem Wolff Rearrangement-Staudinger Cycloaddition. / Synofzik, Judith; Bakulina, Olga; Balabas, Olga; Dar'In, Dmitry; Krasavin, Mikhail.

In: Synthesis (Germany), Vol. 52, No. 2, 16.10.2020, p. 3029-3035.

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

Harvard

Synofzik, J, Bakulina, O, Balabas, O, Dar'In, D & Krasavin, M 2020, 'Catalyst-Free Synthesis of Diastereomerically Pure 3-Sulfonyl azetidin-2-ones via Microwave-Assisted Tandem Wolff Rearrangement-Staudinger Cycloaddition', Synthesis (Germany), vol. 52, no. 2, pp. 3029-3035. https://doi.org/10.1055/s-0040-1707193

APA

Synofzik, J., Bakulina, O., Balabas, O., Dar'In, D., & Krasavin, M. (2020). Catalyst-Free Synthesis of Diastereomerically Pure 3-Sulfonyl azetidin-2-ones via Microwave-Assisted Tandem Wolff Rearrangement-Staudinger Cycloaddition. Synthesis (Germany), 52(2), 3029-3035. https://doi.org/10.1055/s-0040-1707193

Vancouver

Synofzik J, Bakulina O, Balabas O, Dar'In D, Krasavin M. Catalyst-Free Synthesis of Diastereomerically Pure 3-Sulfonyl azetidin-2-ones via Microwave-Assisted Tandem Wolff Rearrangement-Staudinger Cycloaddition. Synthesis (Germany). 2020 Oct 16;52(2):3029-3035. https://doi.org/10.1055/s-0040-1707193

Author

Synofzik, Judith ; Bakulina, Olga ; Balabas, Olga ; Dar'In, Dmitry ; Krasavin, Mikhail. / Catalyst-Free Synthesis of Diastereomerically Pure 3-Sulfonyl azetidin-2-ones via Microwave-Assisted Tandem Wolff Rearrangement-Staudinger Cycloaddition. In: Synthesis (Germany). 2020 ; Vol. 52, No. 2. pp. 3029-3035.

BibTeX

@article{0de0dc5054ad454a83f56a760747fc44,
title = "Catalyst-Free Synthesis of Diastereomerically Pure 3-Sulfonyl azetidin-2-ones via Microwave-Assisted Tandem Wolff Rearrangement-Staudinger Cycloaddition",
abstract = "A wide range of α-diazo-β-ketosulfones have been applied to thermally promoted tandem Wolff rearrangement - Staudinger [2+2] cycloaddition with imines to give polysubstituted β-lactam sulfones. Dia stereomerically pure syn -diastereomers were obtained in good yields and the relative stereochemistry was confirmed by single-crystal X-ray crystallography. These findings significantly expand the scope of this transformation, in contrast to substantial limitations reported previously. Moreover, this methodology enables flexible exploration of new substitution patterns around the privileged β-lactam core for drug design and optimization.",
keywords = "catalyst free, microwave irradiation, Staudinger β-lactam synthesis, Wolff rearrangement, α-diazo-β-ketosulfones, Staudinger beta-lactam synthesis, alpha-diazo-beta-ketosulfones, INHIBITORS",
author = "Judith Synofzik and Olga Bakulina and Olga Balabas and Dmitry Dar'In and Mikhail Krasavin",
note = "Publisher Copyright: {\textcopyright} 2020 Georg Thieme Verlag. All rights reserved.",
year = "2020",
month = oct,
day = "16",
doi = "10.1055/s-0040-1707193",
language = "English",
volume = "52",
pages = "3029--3035",
journal = "Synthesis",
issn = "0039-7881",
publisher = "Georg Thieme Verlag",
number = "2",

}

RIS

TY - JOUR

T1 - Catalyst-Free Synthesis of Diastereomerically Pure 3-Sulfonyl azetidin-2-ones via Microwave-Assisted Tandem Wolff Rearrangement-Staudinger Cycloaddition

AU - Synofzik, Judith

AU - Bakulina, Olga

AU - Balabas, Olga

AU - Dar'In, Dmitry

AU - Krasavin, Mikhail

N1 - Publisher Copyright: © 2020 Georg Thieme Verlag. All rights reserved.

PY - 2020/10/16

Y1 - 2020/10/16

N2 - A wide range of α-diazo-β-ketosulfones have been applied to thermally promoted tandem Wolff rearrangement - Staudinger [2+2] cycloaddition with imines to give polysubstituted β-lactam sulfones. Dia stereomerically pure syn -diastereomers were obtained in good yields and the relative stereochemistry was confirmed by single-crystal X-ray crystallography. These findings significantly expand the scope of this transformation, in contrast to substantial limitations reported previously. Moreover, this methodology enables flexible exploration of new substitution patterns around the privileged β-lactam core for drug design and optimization.

AB - A wide range of α-diazo-β-ketosulfones have been applied to thermally promoted tandem Wolff rearrangement - Staudinger [2+2] cycloaddition with imines to give polysubstituted β-lactam sulfones. Dia stereomerically pure syn -diastereomers were obtained in good yields and the relative stereochemistry was confirmed by single-crystal X-ray crystallography. These findings significantly expand the scope of this transformation, in contrast to substantial limitations reported previously. Moreover, this methodology enables flexible exploration of new substitution patterns around the privileged β-lactam core for drug design and optimization.

KW - catalyst free

KW - microwave irradiation

KW - Staudinger β-lactam synthesis

KW - Wolff rearrangement

KW - α-diazo-β-ketosulfones

KW - Staudinger beta-lactam synthesis

KW - alpha-diazo-beta-ketosulfones

KW - INHIBITORS

UR - http://www.scopus.com/inward/record.url?scp=85089093288&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/85b10cdc-f80f-3bc3-8b0d-461a1090c68d/

U2 - 10.1055/s-0040-1707193

DO - 10.1055/s-0040-1707193

M3 - Article

AN - SCOPUS:85089093288

VL - 52

SP - 3029

EP - 3035

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 2

ER -

ID: 61393422