Enantioselective Synthesis of Cyclopentadienes by Gold(I)‐ Catalyzed Cyclization of 1,3‐Dien‐5‐ynes
2013; Wiley; Volume: 355; Issue: 10 Linguagem: Inglês
10.1002/adsc.201300448
ISSN1615-4169
AutoresAna M. Sanjuán, Patricia García‐García, Manuel A. Fernández‐Rodríguez, Roberto Sanz,
Tópico(s)Cyclopropane Reaction Mechanisms
ResumoAbstract An asymmetric synthesis of elusive chiral cyclopentadienes has been developed by gold(I)‐catalyzed alkoxycyclization of 1,3‐dien‐5‐ynes. The application of these substrates in completely diastereoselective Diels–Alder cycloaddition reactions, which can be carried out in one pot from achiral 1,3‐dien‐5‐ynes, allows the preparation of highly functionalized products bearing five stereogenic centers with high enantiomeric excesses.
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