Deciphering DNA-based asymmetric catalysis through intramolecular Friedel-Crafts alkylations

被引:67
作者
Park, Soyoung [1 ]
Ikehata, Keiichi [1 ]
Watabe, Ryo [1 ]
Hidaka, Yuta [1 ]
Rajendran, Arivazhagan [1 ]
Sugiyama, Hiroshi [1 ,2 ,3 ]
机构
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
[2] Kyoto Univ, Inst Integrated Cell Mat Sci iCeMS, Sakyo Ku, Kyoto 6068502, Japan
[3] Japan Sci & Technol Corp JST, CREST, Chiyoda Ku, Tokyo 1020075, Japan
基金
日本学术振兴会;
关键词
DIELS-ALDER REACTION; ORGANIC-SYNTHESIS; WATER; COMPLEXES; INTERCALATORS; VERSATILE; LIGANDS;
D O I
10.1039/c2cc35625b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We describe asymmetric intramolecular Friedel-Crafts alkylations with a DNA-based hybrid catalyst and propose a plausible binding model. This study shows promise for studying relationships between the helical chirality of DNA and enantioselectivity of the chemical reaction.
引用
收藏
页码:10398 / 10400
页数:3
相关论文
共 35 条
[1]   A journey across recent advances in catalytic and stereoselective alkylation of indoles [J].
Bandini, M ;
Melloni, A ;
Tommasi, S ;
Umani-Ronchi, A .
SYNLETT, 2005, (08) :1199-1222
[2]   The influence of chiral auxiliaries and catalysts on the selectivity of intramolecular conjugate additions of pyrrole to N-tethered Michael acceptors [J].
Banwell, MG ;
Beck, DAS ;
Smith, JA .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (02) :157-159
[3]   DNA-based asymmetric catalysis: Sequence-dependent rate acceleration and enantioselectivity [J].
Boersma, Arnold J. ;
Klijn, Jaap E. ;
Feringa, Ben L. ;
Roelfes, Gerard .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (35) :11783-11790
[4]   α,β-unsaturated 2-acyl imidazoles as a practical class of dienophiles for the DNA-Based catalytic asymmetric diels-alder reaction in water [J].
Boersma, Arnold J. ;
Feringa, Ben L. ;
Roelfes, Gerard .
ORGANIC LETTERS, 2007, 9 (18) :3647-3650
[5]  
Boersma AJ, 2010, NAT CHEM, V2, P991, DOI [10.1038/NCHEM.819, 10.1038/nchem.819]
[6]   DNA-based asymmetric catalysis [J].
Boersma, Arnold J. ;
Megens, Rik P. ;
Feringa, Ben L. ;
Roelfes, Gerard .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (06) :2083-2092
[7]   Enantioselective Friedel-Crafts Reactions in Water Using a DNA-Based Catalyst [J].
Boersma, Arnold J. ;
Feringa, Ben L. ;
Roelfes, Gerard .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (18) :3346-3348
[8]   DNA-Based catalytic enantioselective Michael reactions in water [J].
Coquiere, David ;
Feringa, Ben L. ;
Roelfes, Gerard .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (48) :9308-9311
[9]   On the Role of DNA in DNA-based Catalytic Enantioselective Conjugate Addition Reactions [J].
Dijk, Ewold W. ;
Boersma, Arnold J. ;
Feringa, Ben L. ;
Roelfes, Gerard .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (17) :3868-3873
[10]   DNA-based hydrolytic kinetic resolution of epoxides [J].
Dijk, Ewold W. ;
Feringa, Ben L. ;
Roelfes, Gerard .
TETRAHEDRON-ASYMMETRY, 2008, 19 (20) :2374-2377