Diisopropoxyaluminium trifluoroacetate/4-nitrobenzaldehyde - A new Oppenauer oxidation system for accelerated oxidation of secondary alcohols to the corresponding ketones

被引:19
作者
Akamanchi, KG
Chaudhari, BA
机构
[1] Pharmaceut. and Fine Chem. Division, Department of Chemical Technology, University of Mumbai, Matunga
关键词
D O I
10.1016/S0040-4039(97)01623-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical, efficient and accelerated oxidation of secondary alcohols to the corresponding ketones has been achieved at rt in high yields by a modified Oppenauer oxidation system using diisopropoxyaluminium trifluoroacetate as catalyst and 4-nitrobenzaldehyde as a hydride acceptor. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:6925 / 6928
页数:4
相关论文
共 18 条
[1]   Oxidation of alcohols with ketones [J].
Adkins, H ;
Franklin, RC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1941, 63 :2381-2383
[2]  
Akamanchi KG, 1997, SYNLETT, P371
[3]   Ruthenium-catalyzed Oppenauer-type oxidation of 3 beta-hydroxy steroids. A highly efficient entry into the steroidal hormones with 4-en-3-one functionality [J].
Almeida, MLS ;
Kocovsky, P ;
Backvall, JE .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (19) :6587-6590
[4]   MAGNESIUM-OPPENAUER OXIDATION OF ALCOHOLS TO ALDEHYDES AND KETONES [J].
BYRNE, B ;
KARRAS, M .
TETRAHEDRON LETTERS, 1987, 28 (07) :769-772
[5]   MEERWEIN-PONNDORF-VERLEY REDUCTIONS AND OPPENAUER OXIDATIONS - AN INTEGRATED APPROACH [J].
DEGRAAUW, CF ;
PETERS, JA ;
VANBEKKUM, H ;
HUSKENS, J .
SYNTHESIS-STUTTGART, 1994, (10) :1007-1017
[6]  
DJERASSI C, 1951, ORG REACTIONS, V6, P207
[7]  
Hawkins EGE, 1944, J CHEM SOC, P411
[8]   The elements of the adrenal cortex and related substances 50 Announcement - Simple partial synthesis of substance L and pregnen-(5)-diol-(3 beta, 17 beta)-on-(20) [J].
Hegner, P ;
Reichstein, T .
HELVETICA CHIMICA ACTA, 1941, 24 :828-844
[9]   RATE ENHANCEMENT OF "MEERWEIN-PONNDORF-VERLEY-OPPENHAUER REACTION IN PRESENCE OF PROTON ACIDS [J].
KOW, R ;
NYGREN, R ;
RATHKE, MW .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (05) :826-827
[10]   OXIDATION OF SECONDARY ALCOHOLS OVER HYDROUS ZIRCONIUM(IV) OXIDE [J].
KUNO, H ;
TAKAHASHI, K ;
SHIBAGAKI, M ;
SHIMAZAKI, K ;
MATSUSHITA, H .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (07) :1943-1946