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Functionalized 1‐Alkoxy‐1,3‐dienes: Their Preparation and Applications in Synthetic Organic Chemistry
Author(s) -
Deagostino Annamaria,
Prandi Cristina,
Zavattaro Chiara,
Venturello Paolo
Publication year - 2006
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.200500944
Subject(s) - chemistry , bifunctional , reagent , alkoxy group , electrophile , stille reaction , intramolecular force , organic synthesis , organic chemistry , cycloaddition , combinatorial chemistry , catalysis , alkyl
The reaction of various α,β‐unsaturated acetals with two equivalents of the Schlosser reagent LIC‐KOR [equimolar mixture of BuLi (LIC), and t BuOK (KOR)] gives 1‐metalated (1 E )‐1‐alkoxy‐1,3‐dienes. These products can be transformed into trienic derivatives that are apt to participate in intramolecular Diels–Alder (IMDA) cycloaddition reactions, and can also be transformed into bifunctional (γ‐halo‐α‐carbonyl) reagents. Moreover, the metalated dienes can be readily functionalized with suitable electrophiles to afford products that have been found to be useful reagents for the Stille and Suzuki cross‐coupling reactions or arylated according to the conditions of the Heck process. Other significant syntheses of dienic and polyenic structures are reported along with some of their applications in organic synthesis. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)