Highly selective 1,3-dipolar cycloadditions of captodative olefins 1-acetylvinyl carboxylates to diverse dipoles

Arumugam Nagarajan; Gerardo Zepeda; Joaquín Tamariz

doi:10.1016/0040-4039(96)01546-8

Highly selective 1,3-dipolar cycloadditions of captodative olefins 1-acetylvinyl carboxylates to diverse dipoles

Arumugam Nagarajan, Gerardo Zepeda, Joaquín Tamariz

Escuela Nacional de Ciencias Biológicas (ENCB)

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

23 Scopus citations

Abstract

Regioselective 1,3-dipolar cycloadditions of captodative 1-acetylvinyl p-nitrobenzoyloxy (1a) with propionitrile oxide, diphenylnitrile imine and diazoalkanes provided the corresponding 5-acetyl- isoxazoles and pyrazoles. Evidence to support the formation of the initial cycloadducts was obtained. The addition of nitrones also proved to be highly regio- and stereoselective.

Original language	English
Pages (from-to)	6835-6838
Number of pages	4
Journal	Tetrahedron Letters
Volume	37
Issue number	38
DOIs	https://doi.org/10.1016/0040-4039(96)01546-8
State	Published - 16 Sep 1996

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title = "Highly selective 1,3-dipolar cycloadditions of captodative olefins 1-acetylvinyl carboxylates to diverse dipoles",

abstract = "Regioselective 1,3-dipolar cycloadditions of captodative 1-acetylvinyl p-nitrobenzoyloxy (1a) with propionitrile oxide, diphenylnitrile imine and diazoalkanes provided the corresponding 5-acetyl- isoxazoles and pyrazoles. Evidence to support the formation of the initial cycloadducts was obtained. The addition of nitrones also proved to be highly regio- and stereoselective.",

author = "Arumugam Nagarajan and Gerardo Zepeda and Joaqu{\'i}n Tamariz",

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T1 - Highly selective 1,3-dipolar cycloadditions of captodative olefins 1-acetylvinyl carboxylates to diverse dipoles

AU - Nagarajan, Arumugam

AU - Zepeda, Gerardo

AU - Tamariz, Joaquín

PY - 1996/9/16

Y1 - 1996/9/16

N2 - Regioselective 1,3-dipolar cycloadditions of captodative 1-acetylvinyl p-nitrobenzoyloxy (1a) with propionitrile oxide, diphenylnitrile imine and diazoalkanes provided the corresponding 5-acetyl- isoxazoles and pyrazoles. Evidence to support the formation of the initial cycloadducts was obtained. The addition of nitrones also proved to be highly regio- and stereoselective.

AB - Regioselective 1,3-dipolar cycloadditions of captodative 1-acetylvinyl p-nitrobenzoyloxy (1a) with propionitrile oxide, diphenylnitrile imine and diazoalkanes provided the corresponding 5-acetyl- isoxazoles and pyrazoles. Evidence to support the formation of the initial cycloadducts was obtained. The addition of nitrones also proved to be highly regio- and stereoselective.

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U2 - 10.1016/0040-4039(96)01546-8

DO - 10.1016/0040-4039(96)01546-8

M3 - Artículo

SN - 0040-4039

VL - 37

SP - 6835

EP - 6838

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 38

ER -

Highly selective 1,3-dipolar cycloadditions of captodative olefins 1-acetylvinyl carboxylates to diverse dipoles

Abstract

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