A convenient protocol for the synthesis of axially chiral Bronsted acids

被引:41
作者
Bartoszek, Michael [2 ]
Beller, Matthias [1 ]
Deutsch, Jens [2 ]
Klawonn, Markus [1 ]
Koeckritz, Angela [2 ]
Nemati, Navid [1 ]
Pews-Davtyan, Anahit [1 ]
机构
[1] Univ Rostock, Leibniz Inst Catalysis, D-18059 Rostock, Germany
[2] Univ Rostock, Leibniz Inst Catalysis, Branch Berlin, D-12489 Berlin, Germany
关键词
Bronsted acid; organocatalysts; H8-BINOL diphosphates; polymer;
D O I
10.1016/j.tet.2007.11.067
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Partially hydrogenated binaphthol monophosphoric acids were prepared via an improved four-step sequence. It is demonstrated that typical protection and deprotection of the phenolic groups are dispensable. The vinyl-substituted derivative has been polymerized to give a novel polymerized organocatalyst. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1316 / 1322
页数:7
相关论文
共 57 条
[1]   Enantioselective aza-Diels-Alder reaction catalyzed by a chiral Bronsted acid: Effect of the additive on the enantioselectivity [J].
Akiyama, T ;
Tamura, Y ;
Itoh, J ;
Morita, H ;
Fuchibe, K .
SYNLETT, 2006, (01) :141-143
[2]   Enantioselective Mannich-type reaction catalyzed by a chiral bronsted acid derived from TADDOL [J].
Akiyama, T ;
Saitoh, Y ;
Morita, H ;
Fuchibe, K .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) :1523-1526
[3]   Chiral Bronsted acid catalyzed enantioselective hydrophosphonylation of imines:: Asymmetric synthesis of α-amino phosphonates [J].
Akiyama, T ;
Morita, H ;
Itoh, J ;
Fuchibe, K .
ORGANIC LETTERS, 2005, 7 (13) :2583-2585
[4]   Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid [J].
Akiyama, T ;
Itoh, J ;
Yokota, K ;
Fuchibe, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) :1566-1568
[5]   Chiral Bronsted acid-catalyzed inverse electron-demand aza Diels-Alder reaction [J].
Akiyama, Takahiko ;
Morita, Hisashi ;
Fuchibe, Kohei .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (40) :13070-13071
[6]   Recent progress in chiral Bronsted acid catalysis [J].
Akiyama, Takahiko ;
Itoh, Junji ;
Fuchibe, Kohei .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) :999-1010
[7]  
[Anonymous], 2013, ANGEW CHEM, V125, P4315, DOI DOI 10.1002/1521-3757(20001117)112:22
[8]   Synthesis of 2-substituted-benzothiazoles by palladium-catalyzed intramolecular cyclization of o-bromophenylthioureas and o-bromophenylthioamides [J].
Benedí, C ;
Bravo, F ;
Uriz, P ;
Fernández, E ;
Claver, C ;
Castillón, S .
TETRAHEDRON LETTERS, 2003, 44 (32) :6073-6077
[9]   Rhodium-catalyzed asymmetric conjugate additions of boronic acids using monodentate phosphoramidite ligands [J].
Boiteau, JG ;
Imbos, F ;
Minnaard, AJ ;
Feringa, BL .
ORGANIC LETTERS, 2003, 5 (05) :681-684
[10]   Novel asymmetric alkylation of aromatic aldehydes with triethylaluminum catalyzed by titanium (1,1'-bi-2-naphthol) and titanium (5,5',6,6',7,7',8,8'-octahydro-1,1'-bi-2-naphthol) complexes [J].
Chan, ASC ;
Zhang, FY ;
Yip, CW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (17) :4080-4081