Convenient Approach to 2-Substituted (Thio)morpholin-3-ones from alpha-Diazoacetates via X-H Carbene Insertion - Lactamization Sequence

Research output

Abstract

Stepwise coupling of N-Boc-protected beta-aminoethanols or beta-mercaptoethylamines with various alpha-diazoacetates provides a new, unified approach to constructing (thio)morpholin-3-ones. The process involves a Rh-2(esp)(2)-catalyzed X-H insertion reaction, Boc group removal and ambient-temperature lactamization and is conveniently conducted in one-pot format.

Original languageEnglish
Number of pages8
JournalEuropean Journal of Organic Chemistry
Issue number45
Early online date11 Oct 2019
DOIs
Publication statusPublished - 18 Nov 2019

Cite this

@article{7d055cb611474f2ead92cac40d6b4053,
title = "Convenient Approach to 2-Substituted (Thio)morpholin-3-ones from alpha-Diazoacetates via X-H Carbene Insertion - Lactamization Sequence",
abstract = "Stepwise coupling of N-Boc-protected beta-aminoethanols or beta-mercaptoethylamines with various alpha-diazoacetates provides a new, unified approach to constructing (thio)morpholin-3-ones. The process involves a Rh-2(esp)(2)-catalyzed X-H insertion reaction, Boc group removal and ambient-temperature lactamization and is conveniently conducted in one-pot format.",
keywords = "Diazo compounds, Diazo transfer, Homogeneous catalysis, Insertion, Lactamization, O-H, N-H, CYSTEINE, ACCESS",
author = "Igor Solovyov and Dmitry Dar'in and Mikhail Krasavin",
year = "2019",
month = "11",
day = "18",
doi = "10.1002/ejoc.201901238",
language = "Английский",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley-Blackwell",
number = "45",

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TY - JOUR

T1 - Convenient Approach to 2-Substituted (Thio)morpholin-3-ones from alpha-Diazoacetates via X-H Carbene Insertion - Lactamization Sequence

AU - Solovyov, Igor

AU - Dar'in, Dmitry

AU - Krasavin, Mikhail

PY - 2019/11/18

Y1 - 2019/11/18

N2 - Stepwise coupling of N-Boc-protected beta-aminoethanols or beta-mercaptoethylamines with various alpha-diazoacetates provides a new, unified approach to constructing (thio)morpholin-3-ones. The process involves a Rh-2(esp)(2)-catalyzed X-H insertion reaction, Boc group removal and ambient-temperature lactamization and is conveniently conducted in one-pot format.

AB - Stepwise coupling of N-Boc-protected beta-aminoethanols or beta-mercaptoethylamines with various alpha-diazoacetates provides a new, unified approach to constructing (thio)morpholin-3-ones. The process involves a Rh-2(esp)(2)-catalyzed X-H insertion reaction, Boc group removal and ambient-temperature lactamization and is conveniently conducted in one-pot format.

KW - Diazo compounds

KW - Diazo transfer

KW - Homogeneous catalysis

KW - Insertion

KW - Lactamization

KW - O-H

KW - N-H

KW - CYSTEINE

KW - ACCESS

U2 - 10.1002/ejoc.201901238

DO - 10.1002/ejoc.201901238

M3 - статья

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 45

ER -