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Progress towards the Stereoselective Synthesis of 3,6‐Disubstituted 1,2‐Diamino‐4‐cyclohexenes by Ring Closing Metathesis Reaction
Author(s) -
Grilli Stefano,
Martelli Gianluca,
Savoia Diego,
Zazzetta Carla
Publication year - 2002
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/1615-4169(200212)344:10<1068::aid-adsc1068>3.0.co;2-s
Subject(s) - chemistry , aminal , metathesis , ring closing metathesis , diastereomer , formaldehyde , stereoselectivity , trifluoroacetic acid , ruthenium , yield (engineering) , derivative (finance) , stereochemistry , salt metathesis reaction , dihydroxylation , toluene , nitroethane , medicinal chemistry , organic chemistry , enantioselective synthesis , catalysis , polymerization , materials science , economics , financial economics , metallurgy , polymer
The ring closing metathesis of 4( R ),5( R )‐bis[1( S )‐phenylethylamino]‐3,6‐diethenyl‐1,7‐octadiene required the preliminary formation of the cyclic formaldehyde aminal, then the use of the Grubbs' ruthenium benzylidene complex (10 mol %) in refluxing toluene in the presence of 2 equivalents of trifluoroacetic acid. The cyclic aminal was cleaved in situ after the cyclisation step, so that the final product was the 1,2‐diamino‐3,6‐diethenylcyclohex‐4‐ene derivative. The predominant C 1 ‐symmetric diastereomer was isolated with 48% yield.