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DOI: 10.1055/s-2007-992471
A Novel Complementary Synthesis of Multisubstituted Cyclopentenones via [3+2] Cyclization
Contributor(s):Paul Knochel, Tobias ThalerUniversidad de Oviedo, Spain
A General and Regioselective Synthesis of Cyclopentenone Derivatives through Nickel(0)-Mediated [3+2] Cyclization of Alkenyl Fischer Carbene Complexes and Internal Alkynes
J. Am. Chem. Soc. 2007, 129: 14422-14426
Publication History
Publication Date:
23 January 2008 (online)
Key words
nickel(0) catalysis - Fischer alkenylcarbene complexes - [3+2] cyclization - trisubstituted cyclopentenones
Significance
The formal [3+2]-cycloaddition reaction between an alkenyl-Fischer carbene complex and internal alkynes was found to offer a straightforward access to trisubstituted cyclopent-2-enones with a novel substitution pattern that cannot be easily accessed by conventional methods.
Comment
This highly regioselective and general protocol for the synthesis of trisubstituted cyclopent-2-enones complements the existing approaches, that is, the Nazarov and Pauson-Khand cyclizations, by giving access to substitution patterns. The cyclopentenones derived from the boron- and tin-alkynes may serve as important building blocks, as they can be further modified in subsequent Stille and Suzuki cross-coupling reactions.