4-tert-Butoxy-1-ethoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene. A New Diene and its Application to the Synthesis of gamma-Alkylidenetetronic Acids

Thi Hong Van Nguyen; Bui Duy  Cam; Zafar Ahmed; Peter Langer

doi:10.5560/ZNB.2013-3060

4-tert-Butoxy-1-ethoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene. A New Diene and its Application to the Synthesis of gamma-Alkylidenetetronic Acids

Thi Hong Van Nguyen
, Bui Duy Cam
, Zafar Ahmed
, Peter Langer^*

^*Tämän työn vastaava kirjoittaja

Tutkimustuotos: Artikkeli › Tieteellinen › vertaisarvioitu

Abstrakti

A new approach to gamma-alkylidenetetronic acids is reported which is based on Me3SiOTf-catalyzed [3 + 2] cyclization of 4-tert-butoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene with oxalyl chloride, orthogonal protection of the alpha-hydroxy group by benzylation and subsequent deprotection of the beta-hydroxy group.

Alkuperäiskieli	Englanti
Sivut	836-840
Sivumäärä	5
Julkaisu	Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
Vuosikerta	68
Numero	7
DOI - pysyväislinkit	https://doi.org/10.5560/ZNB.2013-3060
Tila	Julkaistu - heinäk. 2013
OKM-julkaisutyyppi	A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä

Rahoitus

Financial support from the Ministry of Education of Vietnam (scholarship for V.T.H.N.), the State of Mecklenburg-Vorponunern (Landesgraduiertenstipendium for Z. A. and Landesforschungsschwerpunkt 'Neue Wirkstoffe und Screeningverfahren') and from the Deutsche Forschungsgemeinschaft is gratefully acknowledged.

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10.5560/ZNB.2013-3060

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title = "4-tert-Butoxy-1-ethoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene. A New Diene and its Application to the Synthesis of gamma-Alkylidenetetronic Acids",

abstract = "A new approach to gamma-alkylidenetetronic acids is reported which is based on Me3SiOTf-catalyzed [3 + 2] cyclization of 4-tert-butoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene with oxalyl chloride, orthogonal protection of the alpha-hydroxy group by benzylation and subsequent deprotection of the beta-hydroxy group.",

keywords = "Butenolides, Cyclizations, O-Heterocycles, Oxalic Acid, Silyl Enol Ethers, CROSS-COUPLING REACTIONS, STEREOSELECTIVE-SYNTHESIS, EFFICIENT SYNTHESIS, ASCORBIC-ACID, ALKYLIDENEBUTENOLIDES, CYCLIZATION, CHEMISTRY, ETHERS",

author = "\{Van Nguyen\}, \{Thi Hong\} and Cam, \{Bui Duy\} and Zafar Ahmed and Peter Langer",

year = "2013",

month = jul,

doi = "10.5560/ZNB.2013-3060",

language = "English",

volume = "68",

pages = "836--840",

journal = "Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences",

issn = "0932-0776",

publisher = "Walter de Gruyter GmbH",

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4-tert-Butoxy-1-ethoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene. A New Diene and its Application to the Synthesis of gamma-Alkylidenetetronic Acids. / Van Nguyen, Thi Hong; Cam, Bui Duy; Ahmed, Zafar et al.
julkaisussa: Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, Vuosikerta 68, Nro 7, 07.2013, s. 836-840.

Tutkimustuotos: Artikkeli › Tieteellinen › vertaisarvioitu

TY - JOUR

T1 - 4-tert-Butoxy-1-ethoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene. A New Diene and its Application to the Synthesis of gamma-Alkylidenetetronic Acids

AU - Van Nguyen, Thi Hong

AU - Cam, Bui Duy

AU - Ahmed, Zafar

AU - Langer, Peter

PY - 2013/7

Y1 - 2013/7

N2 - A new approach to gamma-alkylidenetetronic acids is reported which is based on Me3SiOTf-catalyzed [3 + 2] cyclization of 4-tert-butoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene with oxalyl chloride, orthogonal protection of the alpha-hydroxy group by benzylation and subsequent deprotection of the beta-hydroxy group.

AB - A new approach to gamma-alkylidenetetronic acids is reported which is based on Me3SiOTf-catalyzed [3 + 2] cyclization of 4-tert-butoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene with oxalyl chloride, orthogonal protection of the alpha-hydroxy group by benzylation and subsequent deprotection of the beta-hydroxy group.

KW - Butenolides

KW - Cyclizations

KW - O-Heterocycles

KW - Oxalic Acid

KW - Silyl Enol Ethers

KW - CROSS-COUPLING REACTIONS

KW - STEREOSELECTIVE-SYNTHESIS

KW - EFFICIENT SYNTHESIS

KW - ASCORBIC-ACID

KW - ALKYLIDENEBUTENOLIDES

KW - CYCLIZATION

KW - CHEMISTRY

KW - ETHERS

U2 - 10.5560/ZNB.2013-3060

DO - 10.5560/ZNB.2013-3060

M3 - Article

SN - 0932-0776

VL - 68

SP - 836

EP - 840

JO - Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

JF - Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

IS - 7

ER -

4-tert-Butoxy-1-ethoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene. A New Diene and its Application to the Synthesis of gamma-Alkylidenetetronic Acids

Abstrakti

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