α-Acyl-α-diazoacetates in Transition-Metal-Free β-Lactam Synthesis

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1 Citation (Scopus)

Abstract

Thermally promoted reaction of α-acyl-α-diazoacetates with imines has been investigated. The transformation, earlier reported predominantly under transition metal catalyzed conditions, delivers α-alkoxycarbonyl-substituted β-lactams with outstanding diastereoselectivity. DFT calculations performed in order to evaluate energetically feasible reaction pathways revealed the intermediacy of 1,3-oxazin-4-one intermediates hitherto never implicated in the Staudinger synthesis of β-lactams.

Original languageEnglish
Pages (from-to)12101-12110
JournalJournal of Organic Chemistry
Volume84
Issue number18
Early online date21 Aug 2019
DOIs
Publication statusPublished - 20 Sep 2019

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Lactams
Transition metals
Imines
Discrete Fourier transforms

Scopus subject areas

  • Organic Chemistry

Cite this

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title = "α-Acyl-α-diazoacetates in Transition-Metal-Free β-Lactam Synthesis",
abstract = "Thermally promoted reaction of α-acyl-α-diazoacetates with imines has been investigated. The transformation, earlier reported predominantly under transition metal catalyzed conditions, delivers α-alkoxycarbonyl-substituted β-lactams with outstanding diastereoselectivity. DFT calculations performed in order to evaluate energetically feasible reaction pathways revealed the intermediacy of 1,3-oxazin-4-one intermediates hitherto never implicated in the Staudinger synthesis of β-lactams.",
keywords = "CASTAGNOLI-CUSHMAN REACTION, PRODUCT SPACE, CYCLOADDITION, ACYLKETENES, IMINES",
author = "Judith Synofzik and Dmitry Dar'In and Novikov, {Mikhail S.} and Grigory Kantin and Olga Bakulina and Mikhail Krasavin",
year = "2019",
month = "9",
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AU - Synofzik, Judith

AU - Dar'In, Dmitry

AU - Novikov, Mikhail S.

AU - Kantin, Grigory

AU - Bakulina, Olga

AU - Krasavin, Mikhail

PY - 2019/9/20

Y1 - 2019/9/20

N2 - Thermally promoted reaction of α-acyl-α-diazoacetates with imines has been investigated. The transformation, earlier reported predominantly under transition metal catalyzed conditions, delivers α-alkoxycarbonyl-substituted β-lactams with outstanding diastereoselectivity. DFT calculations performed in order to evaluate energetically feasible reaction pathways revealed the intermediacy of 1,3-oxazin-4-one intermediates hitherto never implicated in the Staudinger synthesis of β-lactams.

AB - Thermally promoted reaction of α-acyl-α-diazoacetates with imines has been investigated. The transformation, earlier reported predominantly under transition metal catalyzed conditions, delivers α-alkoxycarbonyl-substituted β-lactams with outstanding diastereoselectivity. DFT calculations performed in order to evaluate energetically feasible reaction pathways revealed the intermediacy of 1,3-oxazin-4-one intermediates hitherto never implicated in the Staudinger synthesis of β-lactams.

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KW - PRODUCT SPACE

KW - CYCLOADDITION

KW - ACYLKETENES

KW - IMINES

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JO - Journal of Organic Chemistry

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