A convenient route to both enantiomers of endo-2-benzonorbornenol via lipase catalysed resolution of the racemic mixture

被引:7
作者
Fernández, F
Garcia-Mera, X [1 ]
Rodríguez-Borges, JE
机构
[1] Univ Santiago de Compostela, Fac Farm, Dept Quim Organ, E-15706 Santiago, Spain
[2] Fac Ciencias, Dept Quim, P-4169007 Porto, Portugal
关键词
D O I
10.1016/S0957-4166(01)00079-9
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Resolution of racemic endo-benzonorbornenol (+/-)-4 was performed using Candida antaretica lipase (Novozym" 435) in benzene (50 degreesC;50 hours) with vinyl acetate as the acyl donor to afford (-)-endo-2-benzonorbornenol (-)-6 and their corresponding (+)-endo-2-benzonorbornenyl acetate (+)-5 in high e.e.s of up to 99'% and workable yields of up to 45-46%. (C) 2001 Elsevier Science Ltd. All rights: reserved.
引用
收藏
页码:365 / 368
页数:4
相关论文
共 11 条
[1]   Kinetic resolution of racemic alpha-hydroxy ketones by lipase-catalyzed irreversible transesterification [J].
Adam, W ;
Diaz, MT ;
Fell, RT ;
SahaMoller, CR .
TETRAHEDRON-ASYMMETRY, 1996, 7 (08) :2207-2210
[2]  
BARLETT PD, 1960, J AM CHEM SOC, V82, P1240
[3]   Enantioselective synthesis of 3-functionalized 2-azabicyclo[2.2.1]hept-5-enes by hetero Diels-Alder addition to cyclopentadiene [J].
Blanco, JM ;
Caamaño, O ;
Fernández, F ;
García-Mera, X ;
López, C ;
Rodríguez, G ;
Rodríguez-Borges, JE ;
Rodríguez-Hergueta, A .
TETRAHEDRON LETTERS, 1998, 39 (31) :5663-5666
[4]   A short, efficient synthesis of the chiral auxiliary (+)-8-phenylneomenthol [J].
Caamaño, O ;
Fernández, F ;
García-Mera, X ;
Rodríguez-Borges, JE .
TETRAHEDRON LETTERS, 2000, 41 (21) :4123-4125
[5]   BRIDGED POLYCYCLIC COMPOUNDS .43. POLAR ADDITION OF DEUTERIUM CHLORIDE AND ACETIC ACID-O-D1 AND -D4 TO BENZONORBORNADIENE [J].
CRISTOL, SJ ;
CAPLE, R .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (09) :2741-&
[6]  
Enders D, 1998, SYNLETT, P721
[7]   Synthesis and characterization of all stereoisomers of 8-phenylmenthol [J].
Fernández, F ;
García-Mera, X ;
López, C ;
Rodríguez, G ;
Rodríguez-Borges, JE .
TETRAHEDRON-ASYMMETRY, 2000, 11 (23) :4805-4815
[8]   Are both the (R)- and the (S)-MPA esters really needed for the assignment of the absolute configuration of secondary alcohols by NMR?: The use of a single derivative [J].
Latypov, SK ;
Seco, JM ;
Quiñoá, E ;
Riguera, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (05) :877-882
[9]  
Master HE, 1996, TETRAHEDRON LETT, V37, P9253
[10]   A new optical resolution method: Coordinative resolution of mandelic acid esters. The crystal structure of calcium hydrogen (2R,3R)-O,O'-dibenzoyl tartrate-2(R)-(-)-methyl mandelate [J].
Mravik, A ;
Bocskei, Z ;
Katona, Z ;
Markovits, I ;
Pokol, G ;
Menyhard, DK ;
Fogassy, E .
CHEMICAL COMMUNICATIONS, 1996, (16) :1983-1984