Helical mesoporous silica as an inorganic heterogeneous chiral trigger for asymmetric autocatalysis with amplification of enantiomeric excess

被引:58
作者
Kawasaki, Tsuneomi [1 ,2 ]
Araki, Yuko [1 ]
Hatase, Kunihiko [1 ]
Suzuki, Kenta [1 ]
Matsumoto, Arimasa [1 ]
Yokoi, Toshiyuki [3 ]
Kubota, Yoshihiro [4 ]
Tatsumi, Takashi [3 ]
Soai, Kenso [1 ,2 ]
机构
[1] Tokyo Univ Sci, Dept Appl Chem, Shinjuku Ku, Tokyo 1628601, Japan
[2] Tokyo Univ Sci, Res Ctr Chiral, Res Inst Sci & Technol, Shinjuku Ku, Tokyo 1628601, Japan
[3] Tokyo Inst Technol, Chem Resources Lab, Midori Ku, Yokohama, Kanagawa 2268503, Japan
[4] Yokohama Natl Univ, Div Mat Sci & Chem Engn, Hodogaya Ku, Yokohama, Kanagawa 2408501, Japan
基金
日本学术振兴会;
关键词
HIGHLY ENANTIOSELECTIVE SYNTHESIS; ORGANIC-COMPOUND; SOAI REACTION; CATALYSTS; CRYSTALS; ALKANOL; ORIGIN; CONJUNCTION; ADSORPTION; COMPLEXES;
D O I
10.1039/c5cc01750e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Mesoporous silica has been used as a heterogeneous support for catalysts; however, asymmetric induction by the helicity of inorganic mesoporous silica itself has not yet been achieved. P- and M-helical mesoporous silica was found to act as a chiral inorganic trigger for asymmetric autocatalysis to afford (S) and (R)-pyrimidyl alkanol with >99.5% ee, respectively.
引用
收藏
页码:8742 / 8744
页数:3
相关论文
共 60 条
[1]  
[Anonymous], 1999, COMPREHENSIVE ASYMME
[2]   Stochastic aspects of asymmetric autocatalysis and absolute asymmetric synthesis [J].
Barabas, B. ;
Toth, J. ;
Palyi, G. .
JOURNAL OF MATHEMATICAL CHEMISTRY, 2010, 48 (02) :457-489
[3]   Mechanisms of Autocatalysis [J].
Bissette, Andrew J. ;
Fletcher, Stephen P. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (49) :12800-12826
[4]   Asymmetric autocatalysis with organozinc complexes; Elucidation of the reaction pathway [J].
Brown, John M. ;
Gridnev, Ilya ;
Klankermayer, Juergen .
AMPLIFICATION OF CHIRALITY, 2008, 284 :35-65
[5]  
Caglioti L, 2008, CHIM OGGI, V26, P41
[6]   Prediction of Soai Reaction Enantioselectivity Induced by Crystals of N-(2-Thienylcarbonyl)glycine [J].
Carter, Damien J. ;
Rohl, Andrew L. ;
Shtukenberg, Alexander ;
Bian, Shudan ;
Hu, Chunhua ;
Baylon, Lisa ;
Kahr, Bart ;
Mineki, Hiroko ;
Abe, Koichiro ;
Kawasaki, Tsuneomi ;
Soai, Kenso .
CRYSTAL GROWTH & DESIGN, 2012, 12 (04) :2138-2145
[7]   Synthesis and characterization of chiral mesoporous silica [J].
Che, S ;
Liu, Z ;
Ohsuna, T ;
Sakamoto, K ;
Terasaki, O ;
Tatsumi, T .
NATURE, 2004, 429 (6989) :281-284
[8]   Use of chirally modified zeolites and crystals in photochemical asymmetric synthesis [J].
Chong, KCW ;
Sivaguru, J ;
Shichi, T ;
Yoshimi, Y ;
Ramamurthy, V ;
Scheffer, JR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (12) :2858-2859
[9]   Ordered porous materials for emerging applications [J].
Davis, ME .
NATURE, 2002, 417 (6891) :813-821
[10]   Putting the Mechanism of the Soai Reaction to the Test: DFT Study of the Role of Aldehyde and Dialkylzinc Structure [J].
Ercolani, Gianfranco ;
Schiaffino, Luca .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (08) :2619-2626