Asymmetric synthesis of gamma-hydroxy alpha-enones by 1,8-diazabicyclo[5.4.0]undec-7-ene-catalyzed stereoselective rearrangement of chiral alpha-sulfinyl enones.
The asymmetric rearrangement of optically active alpha-sulfinyl enone 1 induced by catalytic DBU and triphenylphosphine gave optically active gamma-hydroxy alpha-enone derivatives (up to 99% ee) in good yield following treatment with aqueous hydrogen peroxide.
Miura
Motofumi
M
School of Pharmacy, Nihon University, 7-7-1, Narashinodai, Funabashi-shi, Chiba 274-8555, Japan. miura.motofumi@nihon-u.ac.jp
Toriyama
Masaharu
M
Kawakubo
Takashi
T
Yasukawa
Ken
K
Takido
Toshio
T
Motohashi
Shigeyasu
S
D001372:Aza Compounds / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006861:Hydrogen Peroxide / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013454:Sulfoxides / Q000737:chemistry*
D001372:Aza Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D007659:Ketones; D013454:Sulfoxides; D006861:Hydrogen Peroxide