Acylation of alcohols with acetic anhydride catalyzed by TaCl5:: Some implications in kinetic resolution

被引:181
作者
Chandrasekhar, S [1 ]
Ramachander, T [1 ]
Takhi, M [1 ]
机构
[1] Indian Inst Chem Technol, Hyderabad 500007, Andhra Pradesh, India
关键词
D O I
10.1016/S0040-4039(98)00465-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
TaCl5 and TaCl5-Silica gel have been effectively used as Lewis acid catalysts for acetylation of alcohols. Also TaCl3-Chiral ligands have been used for kinetic resolution of 2 degrees alcohols albeit in low ees. (C) 1998 Elsevier Science Ltd. All rights reserved.
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页码:3263 / 3266
页数:4
相关论文
共 13 条
[1]   TaCl5-silicagel and TaCl5 as new Lewis acid systems for selective tetrahydropyranylation of alcohols and thioacetalisation, trimerisation and aldolisation of aldehydes. [J].
Chandrasekhar, S ;
Takhi, M ;
Reddy, YR ;
Mohapatra, S ;
Rao, CR ;
Reddy, KV .
TETRAHEDRON, 1997, 53 (44) :14997-15004
[2]   Solvent free N-alkyl and N-arylimides preparation from anhydrides catalyzed by TaCl5 silica gel [J].
Chandrasekhar, S ;
Takhi, M ;
Uma, G .
TETRAHEDRON LETTERS, 1997, 38 (46) :8089-8092
[3]   STUDIES DIRECTED TOWARD THE DESIGN OF CHIRAL ACYLATING AGENTS - THE UTILITY OF CHIRAL N-BENZOYLIMIDES IN ENANTIOSELECTIVE ALCOHOL ACYLATION [J].
EVANS, DA ;
ANDERSON, JC ;
TAYLOR, MK .
TETRAHEDRON LETTERS, 1993, 34 (35) :5563-5566
[4]  
GREEN TW, 1991, PROTECTIVE GROUPS OR
[5]   COBALT(II) CHLORIDE CATALYZED ACYLATION OF ALCOHOLS WITH ACETIC-ANHYDRIDE - SCOPE AND MECHANISM [J].
IQBAL, J ;
SRIVASTAVA, RR .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :2001-2007
[6]   Scandium trifluoromethanesulfonate as an extremely active Lewis acid catalyst in acylation of alcohols with acid anhydrides and mixed anhydrides [J].
Ishihara, K ;
Kubota, M ;
Kurihara, H ;
Yamamoto, H .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (14) :4560-4567
[7]   Montmorillonite K-10 and KSF as remarkable acetylation catalysts [J].
Li, AX ;
Li, TS ;
Ding, TH .
CHEMICAL COMMUNICATIONS, 1997, (15) :1389-1390
[8]  
PROCOPIOU AP, 1996, CHEM COMMUN, P2625
[9]  
RUBLE CJ, 1997, J AM CHEM SOC, V119, P1492
[10]   TRIBUTYLPHOSPHINE-CATALYZED ACYLATIONS OF ALCOHOLS - SCOPE AND RELATED REACTIONS [J].
VEDEJS, E ;
BENNETT, NS ;
CONN, LM ;
DIVER, ST ;
GINGRAS, M ;
LIN, S ;
OLIVER, PA ;
PETERSON, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (25) :7286-7288