1228457-72-4Relevant academic research and scientific papers
An organocatalytic asymmetric nazarov cyclization
Basak, Ashok K.,Shimada, Naoyuki,Bow, William F.,Vicic, David A.,Tius, Marcus A.
supporting information; experimental part, p. 8266 - 8267 (2010/08/04)
An organocatalytic asymmetric Nazarov cyclization of diketoesters that proceeds by means of a dual activation mechanism has been developed. Screening of a number of catalysts led to a new thiourea that incorporates a primary amino group. The method gives rise to cyclic products with two adjacent quaternary asymmetric carbon atoms, one of which is an all-carbon stereocenter, with complete or nearly complete diastereoselectivity and in high or very high enantiomeric excess. A brief and very convenient synthesis of the acyclic diketoester starting materials through nucleophilic addition to a ketene is also described.
