Sonogashira couplings of halo- and epoxy-halo-exo-glycals: Concise entry to carbohydrate-derived enynes

Ana M. Gómez; Aitor Barrio; Ana Pedregosa; Clara Uriel; Serafín Valverde; J. Cristóbal López

doi:10.1002/ejoc.201000170

Sonogashira couplings of halo- and epoxy-halo-exo-glycals: Concise entry to carbohydrate-derived enynes

Ana M. Gómez
, Aitor Barrio
, Ana Pedregosa
, Clara Uriel
, Serafín Valverde
, J. Cristóbal López

CSIC - Instituto de Química Orgánica General IQOG

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

21 Citations (Scopus)

Abstract

Furanose- and pyranose-derived mono- and dihalo-exo-glycals undergo Sonogashira coupling reactions in the presence of Pd catalysts to give carbohydrate-derived enynes in a completely stereoselective manner. On the other hand, a furanose-derived 2, 3-anhydrohalo-exo-glycal, available from D-mannose in five steps, undergoes Pd⁰-catalyzed Sonogashira coupling, leading to 2-deoxyenynes.

Original language	English
Pages (from-to)	2910-2920
Number of pages	11
Journal	European Journal of Organic Chemistry
Issue number	15
DOIs	https://doi.org/10.1002/ejoc.201000170
Publication status	Published - May 2010
Externally published	Yes

Keywords

Carbohydrates
Cross-coupling
Enynes
Glycals
Palladium

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10.1002/ejoc.201000170

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title = "Sonogashira couplings of halo- and epoxy-halo-exo-glycals: Concise entry to carbohydrate-derived enynes",

abstract = "Furanose- and pyranose-derived mono- and dihalo-exo-glycals undergo Sonogashira coupling reactions in the presence of Pd catalysts to give carbohydrate-derived enynes in a completely stereoselective manner. On the other hand, a furanose-derived 2, 3-anhydrohalo-exo-glycal, available from D-mannose in five steps, undergoes Pd0-catalyzed Sonogashira coupling, leading to 2-deoxyenynes.",

keywords = "Carbohydrates, Cross-coupling, Enynes, Glycals, Palladium",

author = "G{\'o}mez, \{Ana M.\} and Aitor Barrio and Ana Pedregosa and Clara Uriel and Seraf{\'i}n Valverde and \{Crist{\'o}bal L{\'o}pez\}, J.",

year = "2010",

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doi = "10.1002/ejoc.201000170",

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T1 - Sonogashira couplings of halo- and epoxy-halo-exo-glycals

T2 - Concise entry to carbohydrate-derived enynes

AU - Gómez, Ana M.

AU - Barrio, Aitor

AU - Pedregosa, Ana

AU - Uriel, Clara

AU - Valverde, Serafín

AU - Cristóbal López, J.

PY - 2010/5

Y1 - 2010/5

N2 - Furanose- and pyranose-derived mono- and dihalo-exo-glycals undergo Sonogashira coupling reactions in the presence of Pd catalysts to give carbohydrate-derived enynes in a completely stereoselective manner. On the other hand, a furanose-derived 2, 3-anhydrohalo-exo-glycal, available from D-mannose in five steps, undergoes Pd0-catalyzed Sonogashira coupling, leading to 2-deoxyenynes.

AB - Furanose- and pyranose-derived mono- and dihalo-exo-glycals undergo Sonogashira coupling reactions in the presence of Pd catalysts to give carbohydrate-derived enynes in a completely stereoselective manner. On the other hand, a furanose-derived 2, 3-anhydrohalo-exo-glycal, available from D-mannose in five steps, undergoes Pd0-catalyzed Sonogashira coupling, leading to 2-deoxyenynes.

KW - Carbohydrates

KW - Cross-coupling

KW - Enynes

KW - Glycals

KW - Palladium

UR - https://www.scopus.com/pages/publications/77952133926

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DO - 10.1002/ejoc.201000170

M3 - Article

AN - SCOPUS:77952133926

SN - 1434-193X

SP - 2910

EP - 2920

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 15

ER -

Sonogashira couplings of halo- and epoxy-halo-exo-glycals: Concise entry to carbohydrate-derived enynes

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Keywords

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