Tandem [2,3]sigmatropic rearrangement of a sulphonium ylide and cyclopropanation of the resulting electron-rich olefin on a 4-methoxy-2-pyrone derivative

P. de March; M. Moreno-Manas; I. Ripoll; F. Florencio; S. García-Blanco; S. Martinez-Carrera

doi:10.1016/S0040-4039(00)84878-9

Tandem [2,3]sigmatropic rearrangement of a sulphonium ylide and cyclopropanation of the resulting electron-rich olefin on a 4-methoxy-2-pyrone derivative

P. de March, M. Moreno-Manas, I. Ripoll, F. Florencio, S. García-Blanco, S. Martinez-Carrera

Departament de Química

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Rhodium catalyzed reaction of 4-methoxy-6-phenylthiomethyl-2-pyrone with dimethyldiazomalonate affords 5-(bis(methoxycarbonyl))(phenylthio)methyl-4-methoxy-6-methylene-5,6- -dihydro-2-pyrone via [2,3]sigmatropic rearrangement of the corresponding sulphur ylide. Cyclopropanation of the 6-methylene double bond occurs by the less hindered side. © 1986.

Idioma original	Anglès
Pàgines (de-a)	3673-3674
Revista	Tetrahedron Letters
Volum	27
Número	31
DOIs	https://doi.org/10.1016/S0040-4039(00)84878-9
Estat de la publicació	Publicada - 1 de gen. 1986

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10.1016/S0040-4039(00)84878-9

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@article{2aac167d6f50424db142f24de03b5fce,

title = "Tandem [2,3]sigmatropic rearrangement of a sulphonium ylide and cyclopropanation of the resulting electron-rich olefin on a 4-methoxy-2-pyrone derivative",

abstract = "Rhodium catalyzed reaction of 4-methoxy-6-phenylthiomethyl-2-pyrone with dimethyldiazomalonate affords 5-(bis(methoxycarbonyl))(phenylthio)methyl-4-methoxy-6-methylene-5,6- -dihydro-2-pyrone via [2,3]sigmatropic rearrangement of the corresponding sulphur ylide. Cyclopropanation of the 6-methylene double bond occurs by the less hindered side. {\textcopyright} 1986.",

author = "\{de March\}, P. and M. Moreno-Manas and I. Ripoll and F. Florencio and S. Garc{\'i}a-Blanco and S. Martinez-Carrera",

year = "1986",

month = jan,

day = "1",

doi = "10.1016/S0040-4039(00)84878-9",

language = "English",

volume = "27",

pages = "3673--3674",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "31",

}

Tandem [2,3]sigmatropic rearrangement of a sulphonium ylide and cyclopropanation of the resulting electron-rich olefin on a 4-methoxy-2-pyrone derivative. / de March, P.; Moreno-Manas, M.; Ripoll, I. et al.
In: Tetrahedron Letters, Vol. 27, Núm. 31, 01.01.1986, pàg. 3673-3674.

Producció científica: Contribució a revista › Article › Recerca › Avaluat per experts

TY - JOUR

T1 - Tandem [2,3]sigmatropic rearrangement of a sulphonium ylide and cyclopropanation of the resulting electron-rich olefin on a 4-methoxy-2-pyrone derivative

AU - de March, P.

AU - Moreno-Manas, M.

AU - Ripoll, I.

AU - Florencio, F.

AU - García-Blanco, S.

AU - Martinez-Carrera, S.

PY - 1986/1/1

Y1 - 1986/1/1

N2 - Rhodium catalyzed reaction of 4-methoxy-6-phenylthiomethyl-2-pyrone with dimethyldiazomalonate affords 5-(bis(methoxycarbonyl))(phenylthio)methyl-4-methoxy-6-methylene-5,6- -dihydro-2-pyrone via [2,3]sigmatropic rearrangement of the corresponding sulphur ylide. Cyclopropanation of the 6-methylene double bond occurs by the less hindered side. © 1986.

AB - Rhodium catalyzed reaction of 4-methoxy-6-phenylthiomethyl-2-pyrone with dimethyldiazomalonate affords 5-(bis(methoxycarbonyl))(phenylthio)methyl-4-methoxy-6-methylene-5,6- -dihydro-2-pyrone via [2,3]sigmatropic rearrangement of the corresponding sulphur ylide. Cyclopropanation of the 6-methylene double bond occurs by the less hindered side. © 1986.

UR - https://www.scopus.com/pages/publications/46149138663

U2 - 10.1016/S0040-4039(00)84878-9

DO - 10.1016/S0040-4039(00)84878-9

M3 - Article

SN - 0040-4039

VL - 27

SP - 3673

EP - 3674

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 31

ER -

Tandem [2,3]sigmatropic rearrangement of a sulphonium ylide and cyclopropanation of the resulting electron-rich olefin on a 4-methoxy-2-pyrone derivative

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