An effective method for allylic oxidation of Delta5-steroids using tert-butyl hydroperoxide.
An allylic oxidation method for Delta(5)-steroids using TBHP as oxidant with a 2-quinoxalinol salen Cu(II) complex as catalyst is reported. A variety of Delta(5)-steroidal substrates are selectively oxidized to the corresponding enones. Excellent yields are achieved (up to 99% under optimized conditions) while significantly reducing reaction times required as compared to other current methods.
Li
Yuancheng
Y
Department of Chemistry and Biochemistry, College of Science and Mathematics, Auburn Univeristy, Auburn, Alabama 36849-5319, USA.
Wu
Xianghong
X
Lee
Tae Bum
TB
Isbell
Eleanor K
EK
Parish
Edward J
EJ
Gorden
Anne E V
AE
D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry; D020122:tert-Butylhydroperoxide / Q000737:chemistry*
D000498:Allyl Compounds; D009942:Organometallic Compounds; D013256:Steroids; D003300:Copper; D020122:tert-Butylhydroperoxide