A Highly Enantioselective Synthesis of the Odorant, 3-hydroxy-4-phenylbutan-2-one. (February 2013)

• Record Type: Journal Article
• Authors: Liang, Sen; Sun, Bao-guo; Tian, Hong-yu; Wang, Ya-ling; Sun, Yu-mei
• Is Part Of: Journal of chemical research. Volume 37:Number 2(2013)
• Page Start: 105
• Page End: 106
• Publication Date: 2013-02
• Subjects: 3-hydroxy-4-phenylbutan-2-one -- 3, 4-epoxy-4-phenylbutan-2-one -- asymmetric epoxidation -- hydrogenolysis; Chemistry -- Research -- Periodicals; Chemistry -- Periodicals; 540.5
• DOI: 10.3184/174751913X13572401996302
• Languages: English
• ISSNs: 1747-5198

Abstract

An efficient and highly enantioselective synthesis of 3-hydroxy-4-phenylbutan-2-one was developed involving the asymmetric epoxidation of an enone and hydrogenolysis of an α, β-epoxyketone. 1-Phenyl-3-buten-2-one was epoxidised with t -butyl hydroperoxide using a chiral La-BINOL-Ph3 P=O complex as the catalyst to give ( 3S, 4R )- or ( 3R, 4S )-3, 4-epoxy-4-phenylbutan-2-one in ~90% yield and 97% ee. The resultant optically active epoxyketone was reduced in the presence of Pd/C (5 mol%) and H2 (3 bar) in THF at room temperature to produce ( S )- or ( R )-3-hydroxy-4-phenylbutan-2-one in ~80% yield with more than 90% enantiomeric excess.