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

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

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
270 KB
Volume
2009
Category
Article
ISSN
1434-193X

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✦ Synopsis

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 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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