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Rapid and Easy Access to ( E )‐1,3‐Enynes, 1,3‐Diynes and Allenes Starting from Propargylic Acetals, Exploiting the Different Reactivity of Lithium and Mixed Lithium–Potassium Organometallic Reagents
Author(s) -
Blangetti Marco,
Deagostino Annamaria,
Rosso Helèna,
Prandi Cristina,
Zavattaro Chiara,
Venturello Paolo
Publication year - 2007
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.200700520
Subject(s) - chemistry , reagent , lithium (medication) , electrophile , potassium , reactivity (psychology) , base (topology) , combinatorial chemistry , selectivity , conjugated system , medicinal chemistry , organic chemistry , catalysis , medicine , mathematical analysis , alternative medicine , mathematics , pathology , endocrinology , polymer
The treatment of propargylic acetals with various lithium and mixed lithium–potassium Schlosser reagents, has allowed a one‐pot synthesis of ( E )‐1,3‐enynes, 1,3‐diynes and allenes, depending on the reaction conditions and the selected base. Various reaction conditions were investigated in order to control the selectivity of the reactions and to obtain pure products. The metallation–elimination sequence in the presence of a suitable electrophile has provided a linear route to functionalized ( E )‐conjugated enynes, diynes and allenes.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)