Enzymatic synthesis of nonracemic inherently chiral calix[4]arenes by lipase-catalysed transesterification

被引:55
作者
Browne, JK
McKervey, MA [1 ]
Pitarch, M
Russell, JA
Millership, JS
机构
[1] Queens Univ Belfast, Sch Chem, Belfast BT9 5AG, Antrim, North Ireland
[2] Queens Univ Belfast, Sch Pharm, Belfast BT9 7BL, Antrim, North Ireland
关键词
D O I
10.1016/S0040-4039(97)10865-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A lipase-catalysed transesterification to effect a desymmetrisation has been used to produce chiral calix[4]arene derivatives with enantiomer excesses (ee) of up to 100%. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1787 / 1790
页数:4
相关论文
共 10 条
[1]  
BOHMER V, 1987, J ORG CHEM, V52, P3200
[2]   ASYMMETRICALLY-SUBSTITUTED CALIX(4)ARENES [J].
BOHMER, V ;
MERKEL, L ;
KUNZ, U .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (12) :896-897
[3]   SYNTHESIS OF CALIX[4]ARENES PRESENTING NO PLANE OF SYMMETRY [J].
CASABIANCA, H ;
ROYER, J ;
SATRALLAH, A ;
TATYC, A ;
VICENS, J .
TETRAHEDRON LETTERS, 1987, 28 (52) :6595-6596
[4]   CALIXARENES .22. SYNTHESIS, PROPERTIES, AND METAL COMPLEXATION OF AMINOCALIXARENES [J].
GUTSCHE, CD ;
NAM, KC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (18) :6153-6162
[5]   CONFORMATIONAL-ANALYSIS OF CALIX[N]ARENES WITH CHIRAL SUBSTITUENTS BY USING CIRCULAR-DICHROISM [J].
IKEDA, A ;
NAGASAKI, T ;
SHINKAI, S .
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 1992, 5 (10) :699-710
[6]   CALIXARENES .3. PREPARATION OF THE 2,4-DINITROPHENYL AND CAMPHORSULFONYL DERIVATIVES OF THE CALIX[8]ARENE FROM PARA-TERT-BUTYLPHENOL [J].
MUTHUKRISHNAN, R ;
GUTSCHE, CD .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (22) :3962-3964
[7]   STEREOSELECTIVE SYNTHESIS AND OPTICAL RESOLUTION OF CHIRAL CALIX[4]ARENES WITH MIXED LIGATING FUNCTIONALITIES [J].
PAPPALARDO, S ;
CACCAMESE, S ;
GIUNTA, L .
TETRAHEDRON LETTERS, 1991, 32 (52) :7747-7750
[8]   CHIRAL CALIXARENE [J].
SHINKAI, S ;
ARIMURA, T ;
SATOH, H ;
MANABE, O .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (19) :1495-1496
[9]   CROSS-LINKED ENZYME CRYSTALS AS ROBUST BIOCATALYSTS [J].
STCLAIR, NL ;
NAVIA, MA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (18) :7314-7316
[10]   A NOVEL-APPROACH TO INHERENTLY CHIRAL CALIX[4]ARENES BY DIRECT INTRODUCTION OF A SUBSTITUENT AT THE META POSITION [J].
VERBOOM, W ;
BODEWES, PJ ;
VANESSEN, G ;
TIMMERMAN, P ;
VANHUMMEL, GJ ;
HARKEMA, S ;
REINHOUDT, DN .
TETRAHEDRON, 1995, 51 (02) :499-512