Synthesis of alkyl nitronates via Mitsunobu condensation

J. R. Falck; Jurong Yu

doi:10.1016/S0040-4039(00)61760-4

Synthesis of alkyl nitronates via Mitsunobu condensation

J. R. Falck, Jurong Yu

Biochemistry

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

23 Scopus citations

Abstract

Nitroalkanes bearing electron-withdrawing or unsaturated substituents at the α-carbon experience exclusive intra- and intermolecular 0-alkylation by alcohols under Mitsunobu condensation conditions furnishing good to excellent yields of alkyl nitronates; in contrast, 1-phenylsulphonyl-1-nitro-3-propanol affords mainly the corresponding cyclopropane.

Original language	English (US)
Pages (from-to)	6723-6726
Number of pages	4
Journal	Tetrahedron Letters
Volume	33
Issue number	45
DOIs	https://doi.org/10.1016/S0040-4039(00)61760-4
State	Published - Nov 3 1992

Keywords

2-Isoxazoline-2-oxide
5,6-dihydro-4H-oxazine-2-oxide
Mitsunobu
Nitronate
Nitronic ester

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)61760-4

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title = "Synthesis of alkyl nitronates via Mitsunobu condensation",

abstract = "Nitroalkanes bearing electron-withdrawing or unsaturated substituents at the α-carbon experience exclusive intra- and intermolecular 0-alkylation by alcohols under Mitsunobu condensation conditions furnishing good to excellent yields of alkyl nitronates; in contrast, 1-phenylsulphonyl-1-nitro-3-propanol affords mainly the corresponding cyclopropane.",

keywords = "2-Isoxazoline-2-oxide, 5,6-dihydro-4H-oxazine-2-oxide, Mitsunobu, Nitronate, Nitronic ester",

author = "Falck, {J. R.} and Jurong Yu",

note = "Funding Information: Acknowledgment. Supported by grants from the USPHS NIH (DK-38226) and the Robert A. Welch Foundation (I-782). Funds for the purchase of a mass spectrometer were provided by NIH (SlO RR05922).",

year = "1992",

month = nov,

day = "3",

doi = "10.1016/S0040-4039(00)61760-4",

language = "English (US)",

volume = "33",

pages = "6723--6726",

journal = "Tetrahedron Letters",

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number = "45",

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TY - JOUR

T1 - Synthesis of alkyl nitronates via Mitsunobu condensation

AU - Falck, J. R.

AU - Yu, Jurong

N1 - Funding Information: Acknowledgment. Supported by grants from the USPHS NIH (DK-38226) and the Robert A. Welch Foundation (I-782). Funds for the purchase of a mass spectrometer were provided by NIH (SlO RR05922).

PY - 1992/11/3

Y1 - 1992/11/3

N2 - Nitroalkanes bearing electron-withdrawing or unsaturated substituents at the α-carbon experience exclusive intra- and intermolecular 0-alkylation by alcohols under Mitsunobu condensation conditions furnishing good to excellent yields of alkyl nitronates; in contrast, 1-phenylsulphonyl-1-nitro-3-propanol affords mainly the corresponding cyclopropane.

AB - Nitroalkanes bearing electron-withdrawing or unsaturated substituents at the α-carbon experience exclusive intra- and intermolecular 0-alkylation by alcohols under Mitsunobu condensation conditions furnishing good to excellent yields of alkyl nitronates; in contrast, 1-phenylsulphonyl-1-nitro-3-propanol affords mainly the corresponding cyclopropane.

KW - 2-Isoxazoline-2-oxide

KW - 5,6-dihydro-4H-oxazine-2-oxide

KW - Mitsunobu

KW - Nitronate

KW - Nitronic ester

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U2 - 10.1016/S0040-4039(00)61760-4

DO - 10.1016/S0040-4039(00)61760-4

M3 - Article

AN - SCOPUS:0026458102

SN - 0040-4039

VL - 33

SP - 6723

EP - 6726

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 45

ER -

Synthesis of alkyl nitronates via Mitsunobu condensation

Abstract

Keywords

ASJC Scopus subject areas

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