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Ring‐Rearrangement‐Metathesis Approach to Polycycles: Substrate‐Controlled Stereochemical Outcome During Grignard Addition
Author(s) -
Kotha Sambasivarao,
Ravikumar Ongolu
Publication year - 2016
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.201600596
Subject(s) - chemistry , metathesis , norbornene , enyne metathesis , moiety , cycloaddition , ruthenium , propargyl , ring (chemistry) , enyne , stereochemistry , grubbs' catalyst , salt metathesis reaction , cleavage (geology) , organic chemistry , catalysis , monomer , geotechnical engineering , fracture (geology) , engineering , polymerization , polymer
A variety of structurally intricate polycycles have been assembled through ruthenium‐catalysed ring‐rearrangement metathesis of norbornene derivatives. The various substrates required for this work were prepared using Diels–Alder reactions and Grignard additions as key steps. Enyne ring‐rearrangement metathesis of a norbornene system containing a propargyl moiety produced a 1,3‐diene; this was then treated with an appropriate dienophile to deliver the corresponding cycloaddition product.