Novel chiral calix[4]arenes by direct asymmetric epoxidation reaction

被引:21
作者
Bonini, Carlo [1 ]
Chiummiento, Lucia [1 ]
Funicello, Maria [1 ]
Lopardo, Maria Teresa [1 ]
Lupattelli, Paolo [1 ]
Laurita, Alessandro [1 ]
Cornia, Andrea [2 ,3 ]
机构
[1] Univ Basilicata, Dipartimento Chim, I-85100 Potenza, Italy
[2] Univ Modena & Reggio Emilia, Dipartimento Chim, I-41100 Modena, Italy
[3] INSTM, I-41100 Modena, Italy
关键词
D O I
10.1021/jo800301m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report the first asymmetric synthesis of trans optically active H C(2) 1,3-bisarylepoxide of calix[4]arene in excellent chemical yield and >99% ee, and its enantiospecific conversion to the corresponding bis-dioxolane.
引用
收藏
页码:4233 / 4236
页数:4
相关论文
共 38 条
[11]   Resolution of inherently chiral calix[4]arenes with AABB and CDCD substitution patterns on the upper and lower rims, respectively [J].
Caccamese, S ;
Bottino, A ;
Cunsolo, F ;
Parlato, S ;
Neri, P .
TETRAHEDRON-ASYMMETRY, 2000, 11 (15) :3103-3112
[12]   Peptido- and glycocalixarenes: Playing with hydrogen bonds around hydrophobic cavities [J].
Casnati, A ;
Sansone, F ;
Ungaro, R .
ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) :246-254
[13]   Synthesis and properties of O-glycosyl calix[4]arenes (calixsugars) [J].
Dondoni, A ;
Marra, A ;
Scherrmann, MC ;
Casnati, A ;
Sansone, F ;
Ungaro, R .
CHEMISTRY-A EUROPEAN JOURNAL, 1997, 3 (11) :1774-1782
[14]  
Eliel E.L., 1987, Org. Synth, V65, P215, DOI [10.15227/orgsyn.065.0215, DOI 10.15227/ORGSYN.065.0215]
[15]  
Farrugia L.J., 1997, J APPL CRYSTALLOGR, V30, P565
[16]   Transglutaminase surface recognition by peptidocalix[4]arene diversomers [J].
Francese, S ;
Cozzolino, A ;
Caputo, L ;
Esposito, C ;
Martino, M ;
Gaeta, C ;
Troisi, F ;
Neri, P .
TETRAHEDRON LETTERS, 2005, 46 (10) :1611-1615
[17]  
Gutsche C.D., 1998, CALIXARENES REVISITE
[18]  
Gutsche C.D., 1989, Calixarenes
[19]   Acid-promoted rearrangement of carbonate functionality anchored to the lower rim of a calix[4]arene skeleton: A new class of chiral calix[4]arene and its chiroptical properties [J].
Hesek, D ;
Inoue, Y ;
Drew, MGB ;
Beer, PD ;
Hembury, GA ;
Ishida, H ;
Aoki, F .
ORGANIC LETTERS, 2000, 2 (15) :2237-2240
[20]   Synthesis and optical resolution of a series of inherently chiral calix[4]crowns with cone and partial cone conformations [J].
Luo, J ;
Zheng, QY ;
Chen, CF ;
Huang, ZT .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (20) :5917-5928