The Use of α-Diazo-γ-butyrolactams in the Büchner-Curtius-Schlotterbeck Reaction of Cyclic Ketones Opens New Entry to Spirocyclic Pyrrolidones

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The Use of α-Diazo-γ-butyrolactams in the Büchner-Curtius-Schlotterbeck Reaction of Cyclic Ketones Opens New Entry to Spirocyclic Pyrrolidones. / Eremeyeva, Maria; Zhukovsky, Daniil ; Dar'in, Dmitry ; Krasavin, Mikhail.

In: Synlett, Vol. 31, No. 10, 1708011, 17.06.2020, p. 982-986.

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

BibTeX

@article{9a28b41d69d7414eb6c2aab6ac54c584,

title = "The Use of α-Diazo-γ-butyrolactams in the B{\"u}chner-Curtius-Schlotterbeck Reaction of Cyclic Ketones Opens New Entry to Spirocyclic Pyrrolidones",

abstract = "The only cyclic α-diazocarbonyl compound employed in the B{\"u}chner-Curtius-Schlotterbeck ring expansion of cyclic ketones to date was α-diazo-γ-butyrolactone. Encouraged by the recent success using α-diazo acetamides in related Tiffeneau-Demjanov type ring expansions, we extended this approach to various α-diazo-γ-butyrolactams, which produced, under BF3 ·OEt2 -promoted conditions, spirocyclic seven-membered ketones. These findings substantially enhance the possibilities offered by cyclic α-diazocarbonyl compounds in constructing privileged spirocyclic scaffolds for drug design.",

keywords = "B{\"u}chner-Curtius-Schlotterbeck reaction, ring expansion, spirocyclic 2-pyrrolidones, α-diazo-γ-butyrolactams, α-diazocarbonyl compounds, RING EXPANSION, alpha-diazocarbonyl compounds, alpha-diazo-gamma-butyrolactams, Buchner-Curtius-Schlotterbeck reaction, HOMOLOGATION",

author = "Maria Eremeyeva and Daniil Zhukovsky and Dmitry Dar'in and Mikhail Krasavin",

year = "2020",

month = jun,

day = "17",

doi = "10.1055/s-0040-1708011",

language = "English",

volume = "31",

pages = "982--986",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "10",

}

RIS

TY - JOUR

T1 - The Use of α-Diazo-γ-butyrolactams in the Büchner-Curtius-Schlotterbeck Reaction of Cyclic Ketones Opens New Entry to Spirocyclic Pyrrolidones

AU - Eremeyeva, Maria

AU - Zhukovsky, Daniil

AU - Dar'in, Dmitry

AU - Krasavin, Mikhail

PY - 2020/6/17

Y1 - 2020/6/17

N2 - The only cyclic α-diazocarbonyl compound employed in the Büchner-Curtius-Schlotterbeck ring expansion of cyclic ketones to date was α-diazo-γ-butyrolactone. Encouraged by the recent success using α-diazo acetamides in related Tiffeneau-Demjanov type ring expansions, we extended this approach to various α-diazo-γ-butyrolactams, which produced, under BF3 ·OEt2 -promoted conditions, spirocyclic seven-membered ketones. These findings substantially enhance the possibilities offered by cyclic α-diazocarbonyl compounds in constructing privileged spirocyclic scaffolds for drug design.

AB - The only cyclic α-diazocarbonyl compound employed in the Büchner-Curtius-Schlotterbeck ring expansion of cyclic ketones to date was α-diazo-γ-butyrolactone. Encouraged by the recent success using α-diazo acetamides in related Tiffeneau-Demjanov type ring expansions, we extended this approach to various α-diazo-γ-butyrolactams, which produced, under BF3 ·OEt2 -promoted conditions, spirocyclic seven-membered ketones. These findings substantially enhance the possibilities offered by cyclic α-diazocarbonyl compounds in constructing privileged spirocyclic scaffolds for drug design.

KW - Büchner-Curtius-Schlotterbeck reaction

KW - ring expansion

KW - spirocyclic 2-pyrrolidones

KW - α-diazo-γ-butyrolactams

KW - α-diazocarbonyl compounds

KW - RING EXPANSION

KW - alpha-diazocarbonyl compounds

KW - alpha-diazo-gamma-butyrolactams

KW - Buchner-Curtius-Schlotterbeck reaction

KW - HOMOLOGATION

UR - http://www.scopus.com/inward/record.url?scp=85086177718&partnerID=8YFLogxK

U2 - 10.1055/s-0040-1708011

DO - 10.1055/s-0040-1708011

M3 - Article

AN - SCOPUS:85086177718

VL - 31

SP - 982

EP - 986

JO - Synlett

JF - Synlett

SN - 0936-5214

IS - 10

M1 - 1708011

ER -

ID: 59742401