Catalyst-Free Synthesis of Diastereomerically Pure 3-Cyanoazetidin-2-ones via Thermally Promoted Tandem Wolff Rearrangement–Staudinger [2+2] Cycloaddition

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Catalyst-Free Synthesis of Diastereomerically Pure 3-Cyanoazetidin-2-ones via Thermally Promoted Tandem Wolff Rearrangement–Staudinger [2+2] Cycloaddition. / Levashova, Ekaterina ; Bakulina, Olga ; Dar'in, Dmitry ; Krasavin, Mikhail.

In: ChemistrySelect, Vol. 6, No. 47, 20.12.2021, p. 13582-13588.

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

BibTeX

@article{62223a4e8fb64b5e97929c3fcb0b8219,

title = "Catalyst-Free Synthesis of Diastereomerically Pure 3-Cyanoazetidin-2-ones via Thermally Promoted Tandem Wolff Rearrangement–Staudinger [2+2] Cycloaddition",

abstract = "Thermally promoted tandem Wolff rearrangement – Staudinger [2+2] cycloaddition of α-cyano-α-diazo ketones and imines afforded 3-cyano-β-lactams in good to excellent yields as one diastereomer. The process represents the first example of generating cyanoketenes via the Wolff rearrangement of diazo compounds. The reaction is virtually insensitive to the substitution pattern in both reaction partners. It afforded high product yields even for imines bearing bulky tertiary alkyl substituents at the imine's nitrogen atom, which is indicative of the reaction proceeding predominantly as the concerted [2+2] cycloaddition rather than stepwise N-acylation – ring closure process. Examples of reductive manipulation of the resulting 3-cyano-β-lactams are provided opening an entry into 3-aminomethyl 2-azetidinones and azetidines.",

keywords = "Beta-lactam, cycloaddition, diastereoselectivity, diazoketonitriles, metal-free, Staudinger synthesis, Wolff rearrangement",

author = "Ekaterina Levashova and Olga Bakulina and Dmitry Dar'in and Mikhail Krasavin",

note = "Publisher Copyright: {\textcopyright} 2021 Wiley-VCH GmbH",

year = "2021",

month = dec,

day = "20",

doi = "10.1002/slct.202103446",

language = "English",

volume = "6",

pages = "13582--13588",

journal = "ChemistrySelect",

issn = "2365-6549",

publisher = "Wiley-Blackwell",

number = "47",

}

RIS

TY - JOUR

T1 - Catalyst-Free Synthesis of Diastereomerically Pure 3-Cyanoazetidin-2-ones via Thermally Promoted Tandem Wolff Rearrangement–Staudinger [2+2] Cycloaddition

AU - Levashova, Ekaterina

AU - Bakulina, Olga

AU - Dar'in, Dmitry

AU - Krasavin, Mikhail

PY - 2021/12/20

Y1 - 2021/12/20

N2 - Thermally promoted tandem Wolff rearrangement – Staudinger [2+2] cycloaddition of α-cyano-α-diazo ketones and imines afforded 3-cyano-β-lactams in good to excellent yields as one diastereomer. The process represents the first example of generating cyanoketenes via the Wolff rearrangement of diazo compounds. The reaction is virtually insensitive to the substitution pattern in both reaction partners. It afforded high product yields even for imines bearing bulky tertiary alkyl substituents at the imine's nitrogen atom, which is indicative of the reaction proceeding predominantly as the concerted [2+2] cycloaddition rather than stepwise N-acylation – ring closure process. Examples of reductive manipulation of the resulting 3-cyano-β-lactams are provided opening an entry into 3-aminomethyl 2-azetidinones and azetidines.

AB - Thermally promoted tandem Wolff rearrangement – Staudinger [2+2] cycloaddition of α-cyano-α-diazo ketones and imines afforded 3-cyano-β-lactams in good to excellent yields as one diastereomer. The process represents the first example of generating cyanoketenes via the Wolff rearrangement of diazo compounds. The reaction is virtually insensitive to the substitution pattern in both reaction partners. It afforded high product yields even for imines bearing bulky tertiary alkyl substituents at the imine's nitrogen atom, which is indicative of the reaction proceeding predominantly as the concerted [2+2] cycloaddition rather than stepwise N-acylation – ring closure process. Examples of reductive manipulation of the resulting 3-cyano-β-lactams are provided opening an entry into 3-aminomethyl 2-azetidinones and azetidines.

KW - Beta-lactam

KW - cycloaddition

KW - diastereoselectivity

KW - diazoketonitriles

KW - metal-free

KW - Staudinger synthesis

KW - Wolff rearrangement

UR - http://www.scopus.com/inward/record.url?scp=85121545362&partnerID=8YFLogxK

U2 - 10.1002/slct.202103446

DO - 10.1002/slct.202103446

M3 - Article

AN - SCOPUS:85121545362

VL - 6

SP - 13582

EP - 13588

JO - ChemistrySelect

JF - ChemistrySelect

SN - 2365-6549

IS - 47

ER -

ID: 90823655