Catalytic deprotection of Acetals in basic solution with a self-assembled supramolecular "Nanozyme"

被引:95
作者
Pluth, Michael D. [1 ]
Bergman, Robert G. [1 ]
Raymond, Kenneth N. [1 ]
机构
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
关键词
cage compounds; homogeneous catalysis; host-guest systems; protecting groups; supramolecular chemistry;
D O I
10.1002/anie.200703371
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Formula Presented) Changing on the inside: Acetals are a commonly used protecting groups for aldehydes and ketones in organic synthesis because of their ease of installation and resistance to cleavage in neutral or basic solution. A self-assembled supramolecular assembly has been shown to catalyze the hydrolysis of acetals and ketals in basic solution (see scheme). © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:8587 / 8589
页数:3
相关论文
共 37 条
[1]  
[Anonymous], ANGEW CHEM
[2]   Mild and chemoselective catalytic deprotection of ketals and acetals using cerium(IV) ammonium nitrate [J].
Ates, A ;
Gautier, A ;
Leroy, B ;
Plancher, JM ;
Quesnel, Y ;
Vanherck, JC ;
Markó, IE .
TETRAHEDRON, 2003, 59 (45) :8989-8999
[3]   Encapsulation and stabilization of reactive aromatic diazonium ions and the tropylium ion within a supramolecular host [J].
Brumaghim, JL ;
Michels, M ;
Pagliero, D ;
Raymond, KN .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (24) :5115-5118
[4]   Hydrophobic chemistry in aqueous solution: Stabilization and stereoselective encapsulation of phosphonium guests in a supramolecular host [J].
Brumaghim, JL ;
Michels, M ;
Raymond, KN .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (22) :4552-4559
[5]   A simple and efficient chemoselective method for the catalytic deprotection of acetals and ketals using bismuth triflate [J].
Carrigan, MD ;
Sarapa, D ;
Smith, RC ;
Wieland, LC ;
Mohan, RS .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (03) :1027-1030
[6]  
Caulder D. L., 1998, ANGEW CHEM, V110, P1940
[7]   Supermolecules by design [J].
Caulder, DL ;
Raymond, KN .
ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (11) :975-982
[8]   Coordination number incommensurate cluster formation, part 21 -: Design, formation and properties of tetrahedral M4L4 and M4L6 supramolecular clusters [J].
Caulder, DL ;
Brückner, C ;
Powers, RE ;
König, S ;
Parac, TN ;
Leary, JA ;
Raymond, KN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (37) :8923-8938
[9]   The rational design of high symmetry coordination clusters [J].
Caulder, DL ;
Raymond, KN .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1999, (08) :1185-1200
[10]  
Caulder DL, 1998, ANGEW CHEM INT EDIT, V37, P1840, DOI 10.1002/(SICI)1521-3773(19980803)37:13/14<1840::AID-ANIE1840>3.0.CO