1210056-55-5Relevant articles and documents
A practical protocol for asymmetric synthesis of wieland-miescher and hajos-parrish ketones catalyzed by a simple chiral primary amine
Xu, Changming,Zhang, Long,Zhou, Pengxin,Luo, Sanzhong,Cheng, Jin-Pei
, p. 1939 - 1945 (2013/07/26)
This article describes a simple chiral primary amine catalyzed efficient and practical protocol for the large-scale synthesis of Wieland-Miescher and Hajos-Parrish ketones as well as their analogues. Georg Thieme Verlag Stuttgart. New York.
Efficient solvent-free robinson annulation protocols for the highly enantioselective synthesis of the wieland-miescher ketone and analogues
Bradshaw, Ben,Etxebarria-Jardi, Gorka,Bonjoch, Josep,Viozquez, Santiago F.,Guillena, Gabriela,Najera, Carmen
supporting information; experimental part, p. 2482 - 2490 (2009/12/29)
A highly efficient (93% overall yield) and enantioselective (94% ee) synthesis of the WielandMiescher ketone (10-g scale) through a solvent-free Robinson annulation procedure is reported. The process involves only 1 mol% triethylamine as the base in the initial Michael process and the organocatalyst N-tosyl-(Sa)-binam-L-prolinamide (2mol%) and benzoic acid (0.5 mol% ) for the intramolecular aldol process. This green protocol is applied to a wide range of valuable building block analogues of the Wieland-Miescher ketone (10 examples). Among these, a noteworthy compound for terpene synthesis is the 8a-allyl derivative, which is prepared in 93% yield and 97% ee in a process allowing the recovery and reutilization of the organocatalyst. Furthermore, a one-pot, two-step process has also been developed.