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Simple Synthetic Transformations of Highly Enantio‐Enriched 4‐Alkyl‐2,5,7‐cyclooctatrienols into Functionalized Bicyclo[4.2.0]octa‐2,4‐dienes and 2,6‐Cyclooctadienones
Author(s) -
Pineschi Mauro,
Del Moro Federica,
Crotti Paolo,
Macchia Franco
Publication year - 2004
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.200400355
Subject(s) - chemistry , alkyl , reagent , domino , phosphoramidite , bicyclic molecule , enantiomeric excess , enantiomer , cascade reaction , organic chemistry , thermal decomposition , combinatorial chemistry , medicinal chemistry , enantioselective synthesis , catalysis , dna , biochemistry , oligonucleotide
4‐Alkyl‐2,5,7‐cyclooctatrienols with high enantiomeric purities (93−96% ee ), obtained by an improved copper‐phosphoramidite‐catalyzed addition of dialkylzinc reagents to cyclooctatetraene monoepoxide, have been subjected to simple and practical manipulations. Simple esterification reactions are able to deliver new functionalized isomeric 8‐alkyl‐7‐acyloxybicyclo[4.2.0]octa‐2,4‐dienes through a domino sequence of rearrangement reactions, in good yields. Moreover, new 4‐alkyl‐substituted‐2,6‐cyclooctadienones with high optical purity can be efficiently obtained from gram‐scale reactions by simple thermal treatment. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)