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Tandem Sequential Ring‐Closing Metathesis/Diels–Alder/Cross‐Metathesis: Formation of Polycyclic Compounds by a New Three‐Component Reaction
Author(s) -
Virolleaud MarieAlice,
Piva Olivier
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.200600946
Subject(s) - chemistry , metathesis , ring closing metathesis , alkene , tandem , salt metathesis reaction , yield (engineering) , diels–alder reaction , propargyl , acyclic diene metathesis , diene , organic chemistry , combinatorial chemistry , catalysis , materials science , natural rubber , composite material , metallurgy , polymerization , polymer
Abstract Polycyclic oxygenated compounds have been generated from penta‐ or hexadienyl propargyl ethers by a new procedure that combines the selective formation of a 1,3‐diene by ring‐closing metathesis (RCM), a Diels–Alder (DA) reaction and subsequent cross‐metathesis (CM) with a chosen alkene, which allows the functionalization of the vinyl group generated during the first step. All these processes can be performed in a one‐pot reaction with a yield of up to 63 %. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)