Tandem RCM-isomerization-cyclopropanation reactions.
A new triple tandem process has been discovered in which simple acyclic substrates can be transformed into bicyclic compounds via RCM-double bond isomerization-cyclopropanation. This process is catalyzed by second generation Grubb's catalyst without the requirement of other reactives or additives. In addition, a one-pot RCM-isomerization reaction followed by cyclopropanation with CHCl3/NaOH allows the synthesis of products related to iNOS (nitric oxide synthase) inhibitors, which are currently under clinical evaluation.
Mallagaray
Alvaro
A
Facultad de Farmacia, Dpto. Química, Universidad San Pablo CEU, Urb. Montepríncipe, ctra. Boadilla km 5,300 Boadilla del Monte, 28668 Madrid, Spain.
Domínguez
Gema
G
Gradillas
Ana
A
Pérez-Castells
Javier
J
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D003521:Cyclopropanes / Q000737:chemistry*; D015394:Molecular Structure; D019001:Nitric Oxide Synthase / Q000037:antagonists & inhibitors*; D013237:Stereoisomerism
D019086:Bridged Bicyclo Compounds, Heterocyclic; D003521:Cyclopropanes; D019001:Nitric Oxide Synthase