Facile Synthesis of Spirocyclic Lactams via [3+2] and [3+3] Aza-Annulation Reactions

Davit Hayrapetyan; Valeriya Stepanova

doi:10.1002/ejoc.202100255

Facile Synthesis of Spirocyclic Lactams via [3+2] and [3+3] Aza-Annulation Reactions

Davit Hayrapetyan
, Valeriya Stepanova

Department of Chemistry

Nazarbayev University

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

4 Citations (Scopus)

Abstract

Spirocyclic pyrrolidones and piperidones were synthesized starting from readily available α-ketolactones and α-ketolactams employing [3+2]- and [3+3]-aza-annulation reactions. Annulation reactions proceeded with good yields and further reduction of the exocyclic C=C double bond of the enamide moiety proceeded with excellent diastereoselectivity. Overall, one C−C and two C−N bonds, as well as three new stereocenters were created in a diastereoselective manner resulting in a fast upbuild of molecular complexity.

Original language	English
Pages (from-to)	2121-2125
Number of pages	5
Journal	European Journal of Organic Chemistry
Volume	2021
Issue number	14
DOIs	https://doi.org/10.1002/ejoc.202100255 https://doi.org/10.1002/ejoc.202100255
Publication status	Published - Apr 15 2021

Funding

This work was supported by Nazarbayev University via FDCRG (Nr. 240919FD3905) and SPG grants to DH and FRIP grant to VS. We thank Ms. Ainur Slamova (NU Core Facilities) for performing NMR and elemental analysis measurements and Mr. Farkhad Tarikhov (NU Core Facilities) for performing NMR measurements.

Keywords

Annulation
Diastereoselectivity
Lactams
Nitrogen heterocycles
Spiro compounds

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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title = "Facile Synthesis of Spirocyclic Lactams via [3+2] and [3+3] Aza-Annulation Reactions",

abstract = "Spirocyclic pyrrolidones and piperidones were synthesized starting from readily available α-ketolactones and α-ketolactams employing [3+2]- and [3+3]-aza-annulation reactions. Annulation reactions proceeded with good yields and further reduction of the exocyclic C=C double bond of the enamide moiety proceeded with excellent diastereoselectivity. Overall, one C−C and two C−N bonds, as well as three new stereocenters were created in a diastereoselective manner resulting in a fast upbuild of molecular complexity.",

keywords = "Annulation, Diastereoselectivity, Lactams, Nitrogen heterocycles, Spiro compounds",

author = "Davit Hayrapetyan and Valeriya Stepanova",

note = "Funding Information: This work was supported by Nazarbayev University via FDCRG (Nr. 240919FD3905) and SPG grants to DH and FRIP grant to VS. We thank Ms. Ainur Slamova (NU Core Facilities) for performing NMR and elemental analysis measurements and Mr. Farkhad Tarikhov (NU Core Facilities) for performing NMR measurements. Publisher Copyright: {\textcopyright} 2021 Wiley-VCH GmbH",

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doi = "10.1002/ejoc.202100255",

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T1 - Facile Synthesis of Spirocyclic Lactams via [3+2] and [3+3] Aza-Annulation Reactions

AU - Hayrapetyan, Davit

AU - Stepanova, Valeriya

N1 - Funding Information: This work was supported by Nazarbayev University via FDCRG (Nr. 240919FD3905) and SPG grants to DH and FRIP grant to VS. We thank Ms. Ainur Slamova (NU Core Facilities) for performing NMR and elemental analysis measurements and Mr. Farkhad Tarikhov (NU Core Facilities) for performing NMR measurements. Publisher Copyright: © 2021 Wiley-VCH GmbH

PY - 2021/4/15

Y1 - 2021/4/15

N2 - Spirocyclic pyrrolidones and piperidones were synthesized starting from readily available α-ketolactones and α-ketolactams employing [3+2]- and [3+3]-aza-annulation reactions. Annulation reactions proceeded with good yields and further reduction of the exocyclic C=C double bond of the enamide moiety proceeded with excellent diastereoselectivity. Overall, one C−C and two C−N bonds, as well as three new stereocenters were created in a diastereoselective manner resulting in a fast upbuild of molecular complexity.

AB - Spirocyclic pyrrolidones and piperidones were synthesized starting from readily available α-ketolactones and α-ketolactams employing [3+2]- and [3+3]-aza-annulation reactions. Annulation reactions proceeded with good yields and further reduction of the exocyclic C=C double bond of the enamide moiety proceeded with excellent diastereoselectivity. Overall, one C−C and two C−N bonds, as well as three new stereocenters were created in a diastereoselective manner resulting in a fast upbuild of molecular complexity.

KW - Annulation

KW - Diastereoselectivity

KW - Lactams

KW - Nitrogen heterocycles

KW - Spiro compounds

UR - https://www.scopus.com/pages/publications/85110562293

UR - https://www.scopus.com/pages/publications/85110562293#tab=citedBy

U2 - 10.1002/ejoc.202100255

DO - 10.1002/ejoc.202100255

M3 - Article

AN - SCOPUS:85110562293

SN - 1434-193X

VL - 2021

SP - 2121

EP - 2125

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 14

ER -

Facile Synthesis of Spirocyclic Lactams via [3+2] and [3+3] Aza-Annulation Reactions

Abstract

Funding

Keywords

ASJC Scopus subject areas

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