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Synthesis of Acyloxy‐Semicyclic Dienes Using an Enyne Metathesis/Ring Closing Metathesis Approach
Author(s) -
Kueh Jui Thiang Brian,
Moodie Lindon W. K.,
Lucas Nigel T.,
Larsen David S.
Publication year - 2015
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.201403482
Subject(s) - enyne metathesis , chemistry , metathesis , ring closing metathesis , enyne , acyclic diene metathesis , salt metathesis reaction , diene , stereochemistry , organic chemistry , combinatorial chemistry , catalysis , polymerization , natural rubber , polymer
An enyne metathesis/ring closing metathesis (EM/RCM) sequence was used to synthesise acyloxy‐semicyclic dienes from an enyne substrate and various vinyl esters. This allowed convenient access to acyloxy‐semicyclic dienes not accessible by cross metathesis alone due to the low reactivity of Fischer carbenes with the termini of 1,3‐dienes. This new approach also provides an alternative method for the synthesis of 1‐acyloxy‐1,3‐dienes which are useful reactants for Diels–Alder cycloadditions.