Asymmetric synthesis of Wieland-Miescher and Hajos-Parrish ketones catalyzed by an amino-acid-derived chiral primary amine.
This paper describes a simple chiral primary amine-catalyzed highly efficient and practical protocol for the synthesis of both Wieland-Miescher ketone and Hajos-Parrish ketone as well as their analogues. The reaction can be conducted in gram scale with 1% mol catalyst loading producing high enantioselectivity (up to 96% ee) and excellent yields (up to 98%). This procedure represents one of the most efficient methods for the synthesis of these versatile chiral building blocks.
Beijing National Laboratory for Molecule Sciences, Institute of Chemistry, the Chinese Academy of Sciences, Beijing, 100190 China.
Pengxin
P
Zhou
Long
L
Zhang
Sanzhong
S
Luo
Jin-Pei
JP
Cheng
D000588:Amines / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D000588:Amines; D000596:Amino Acids; D007659:Ketones