Synthesis of Furanosyl  C ‐1 Glycals through Palladium‐Catalyzed Reactions of a Furanosyl 2,3‐Anhydro‐ exo ‐glycal | Zendy

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

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Synthesis of Furanosyl C ‐1 Glycals through Palladium‐Catalyzed Reactions of a Furanosyl 2,3‐Anhydro‐ exo ‐glycal

Author(s) -

Gómez Ana M.,

Pedregosa Ana,

Barrio Aitor,

Valverde Serafín,

López J. Cristóbal

Publication year - 2009

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200900585

Subject(s) - chemistry , umpolung , glycal , palladium , nucleophile , electrophile , organic chemistry , furanose , catalysis , diethyl malonate , combinatorial chemistry , medicinal chemistry , stereoselectivity , ring (chemistry)

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 Pd 0 it affords a π‐allyl palladium complex that can react with nucleophiles such as amines, ethyl malonate, or vinylstannanes. On the other hand, umpolung of the π‐allyl palladium complex with Et 2 Zn facilitates its reaction with electrophilic aldehydes and ketones.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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