Synthesis of furanosyl C-1 glycals through palladium-catalyzed reactions of a furanosyl 2,3-anhydro-exe-glycal

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

doi:10.1002/ejoc.200900585

Synthesis of furanosyl C-1 glycals through palladium-catalyzed reactions of a furanosyl 2,3-anhydro-exe-glycal

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

CSIC - Instituto de Química Orgánica General IQOG

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

8 Citations (Scopus)

Abstract

A furanose-derived 2,3-anhydro-exo-glycal, readily available from D-mannose in four steps, has proven to be a useful substrate in the preparation of a variety of highly functionalized C-1 glycals. Upon treatment with Pd0 it affords a Tc-allyl palladium, complex that can react with nucleophiles such as amines, ethyl malonate, or vinylstannaries. On the other hand, umpolung of the 71-allyl palladium, complex with Et₂Zn facilitates its reaction with electrophilic aldehydes and. ketones,

Original language	English
Pages (from-to)	4627-4636
Number of pages	10
Journal	European Journal of Organic Chemistry
Issue number	27
DOIs	https://doi.org/10.1002/ejoc.200900585
Publication status	Published - Sept 2009
Externally published	Yes

Keywords

Carbohydrates
Electrophilic substitution
Glycals
Nucleophilic substitution
Palladium
Umpolung

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10.1002/ejoc.200900585

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title = "Synthesis of furanosyl C-1 glycals through palladium-catalyzed reactions of a furanosyl 2,3-anhydro-exe-glycal",

abstract = "A furanose-derived 2,3-anhydro-exo-glycal, readily available from D-mannose in four steps, has proven to be a useful substrate in the preparation of a variety of highly functionalized C-1 glycals. Upon treatment with Pd0 it affords a Tc-allyl palladium, complex that can react with nucleophiles such as amines, ethyl malonate, or vinylstannaries. On the other hand, umpolung of the 71-allyl palladium, complex with Et2Zn facilitates its reaction with electrophilic aldehydes and. ketones,",

keywords = "Carbohydrates, Electrophilic substitution, Glycals, Nucleophilic substitution, Palladium, Umpolung",

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

year = "2009",

month = sep,

doi = "10.1002/ejoc.200900585",

language = "English",

pages = "4627--4636",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

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TY - JOUR

T1 - Synthesis of furanosyl C-1 glycals through palladium-catalyzed reactions of a furanosyl 2,3-anhydro-exe-glycal

AU - Gómez, Ana M.

AU - Pedregosa, Ana

AU - Barrio, Aitor

AU - Valverde, Serafín

AU - Cristóbal López, J.

PY - 2009/9

Y1 - 2009/9

N2 - A furanose-derived 2,3-anhydro-exo-glycal, readily available from D-mannose in four steps, has proven to be a useful substrate in the preparation of a variety of highly functionalized C-1 glycals. Upon treatment with Pd0 it affords a Tc-allyl palladium, complex that can react with nucleophiles such as amines, ethyl malonate, or vinylstannaries. On the other hand, umpolung of the 71-allyl palladium, complex with Et2Zn facilitates its reaction with electrophilic aldehydes and. ketones,

AB - A furanose-derived 2,3-anhydro-exo-glycal, readily available from D-mannose in four steps, has proven to be a useful substrate in the preparation of a variety of highly functionalized C-1 glycals. Upon treatment with Pd0 it affords a Tc-allyl palladium, complex that can react with nucleophiles such as amines, ethyl malonate, or vinylstannaries. On the other hand, umpolung of the 71-allyl palladium, complex with Et2Zn facilitates its reaction with electrophilic aldehydes and. ketones,

KW - Carbohydrates

KW - Electrophilic substitution

KW - Glycals

KW - Nucleophilic substitution

KW - Palladium

KW - Umpolung

UR - https://www.scopus.com/pages/publications/70349194905

U2 - 10.1002/ejoc.200900585

DO - 10.1002/ejoc.200900585

M3 - Article

AN - SCOPUS:70349194905

SN - 1434-193X

SP - 4627

EP - 4636

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 27

ER -

Synthesis of furanosyl C-1 glycals through palladium-catalyzed reactions of a furanosyl 2,3-anhydro-exe-glycal

Abstract

Keywords

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