RETRACTED: A Mechanochemical Approach to Deracemization (Retracted Article)

被引:32
作者
Wiggins, Kelly M. [1 ]
Bielawski, Christopher W. [1 ]
机构
[1] Univ Texas Austin, Dept Chem & Biochem, Univ Stn 1, Austin, TX 78712 USA
关键词
atropisomerism; chiral resolution; mechanochemistry; polymers; ultrasound; ASYMMETRIC TRANSFORMATIONS; ENZYMES; RESOLUTIONS; CATALYSIS; POLYMERS;
D O I
10.1002/anie.201107937
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Good combination: Enantioselective enzymatic hydrolysis was combined with a mechanically facilitated racemization process to prepare (S)-1,1′- binapthol ((S)-binol) in high yield and enantiopurity from a racemic precursor in a single step (see scheme). The enzyme cholesterol esterase stereoselectively hydrolyzes esters of (S)-binol and ultrasound was applied to achieve mechanically facilitated racemization of the precursor material. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:1640 / 1643
页数:4
相关论文
共 41 条
[1]   From molecular mechanochemistry to stress-responsive materials [J].
Black, Ashley L. ;
Lenhardt, Jeremy M. ;
Craig, Stephen L. .
JOURNAL OF MATERIALS CHEMISTRY, 2011, 21 (06) :1655-1663
[2]   Atroposelective synthesis of axially chiral biaryl compounds [J].
Bringmann, G ;
Mortimer, AJP ;
Keller, PA ;
Gresser, MJ ;
Garner, J ;
Breuning, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (34) :5384-5427
[3]  
Bringmann G., 2005, ANGEW CHEM INT EDIT, V117, P5518, DOI 10.1002/ange.200462661
[4]   BINOL: A versatile chiral reagent [J].
Brunel, JM .
CHEMICAL REVIEWS, 2005, 105 (03) :857-897
[5]   Dynamic resolutions in asymmetric synthesis [J].
Caddick, S ;
Jenkins, K .
CHEMICAL SOCIETY REVIEWS, 1996, 25 (06) :447-&
[6]   Mechanically-Induced Chemical Changes in Polymeric Materials [J].
Caruso, Mary M. ;
Davis, Douglas A. ;
Shen, Qilong ;
Odom, Susan A. ;
Sottos, Nancy R. ;
White, Scott R. ;
Moore, Jeffrey S. .
CHEMICAL REVIEWS, 2009, 109 (11) :5755-5798
[7]  
Eliel E. L., 1994, STEREOCHEMISTRY ORGA
[8]  
Faber K., 2004, BIOTRANSFORMATIONS O
[9]   Biasing reaction pathways with mechanical force [J].
Hickenboth, Charles R. ;
Moore, Jeffrey S. ;
White, Scott R. ;
Sottos, Nancy R. ;
Baudry, Jerome ;
Wilson, Scott R. .
NATURE, 2007, 446 (7134) :423-427
[10]   Toward understanding and tailoring the specificity of synthetically useful enzymes [J].
Jones, JB ;
Desantis, G .
ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (02) :99-107