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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)