Enantioselective Enolate Protonations: Friedel-Crafts Reactions with α-Substituted Acrylates

被引:54
作者
Sibi, Mukund P. [1 ]
Coulomb, Julien [1 ]
Stanley, Levi M. [1 ]
机构
[1] N Dakota State Univ, Dept Chem & Mol Biol, Fargo, ND 58105 USA
基金
美国国家科学基金会;
关键词
alkylation; asymmetric catalysis; chiral auxiliaries; enantioselectivity; nitrogen heterocycles;
D O I
10.1002/anie.200804221
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Templates rule: A Zn(NTf2) 2/1 catalyzed tandem Friedel-Crafts alkylation/enantioselective protonation of pyrroles with isoxazolidinone-derived α-substituted a,b-unsaturated imides, provides high levels of rotamer control and enantioselectivity in the tandem sequence, and affords pyrrole derivatives in good-toexcellent yields (68-98%) and enantioselectivities (43-98% ee). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:9913 / 9915
页数:3
相关论文
共 44 条
[1]   Triflic acid-catalyzed highly stereoselective friedel-crafts aminoalkylation of indoles and pyrroles [J].
Abid, Mohammed ;
Teixeira, Liliana ;
Torok, Bela .
ORGANIC LETTERS, 2008, 10 (05) :933-935
[2]   Enantioselective organocatalytic indole alkylations. Design of a new and highly effective chiral amine for iminium catalysis [J].
Austin, JF ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (07) :1172-1173
[3]   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
[4]   TRANSITION STRUCTURES OF THE LEWIS ACID-CATALYZED DIELS-ALDER REACTION OF BUTADIENE WITH ACROLEIN - THE ORIGINS OF SELECTIVITY [J].
BIRNEY, DM ;
HOUK, KN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) :4127-4133
[5]   A Bronsted acid catalyst for the enantioselective protonation reaction [J].
Cheon, Cheol Hong ;
Yamamoto, Hisashi .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) :9246-+
[6]   Enantioselective protonations: fundamental insights and new concepts [J].
Duhamel, L ;
Duhamel, P ;
Plaquevent, JC .
TETRAHEDRON-ASYMMETRY, 2004, 15 (23) :3653-3691
[7]   Enantioselective indole Friedel-Crafts alkylations catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes [J].
Evans, DA ;
Scheidt, KA ;
Fandrick, KR ;
Lam, HW ;
Wu, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10780-10781
[8]   Enantioselective friedel-crafts alkylations catalyzed by Bis(oxazolinyl)pyridine-Scandium(III) triflate complexes [J].
Evans, David A. ;
Fandrick, Keith R. ;
Song, Hyun-Ji ;
Scheidt, Karl A. ;
Xu, Risheng .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (32) :10029-10041
[9]   Rhodium-catalyzed conjugate addition-enantioselective protonation:: The synthesis of α,α'-dibenzyl esters [J].
Frost, Christopher G. ;
Penrose, Stephen D. ;
Lambshead, Kim ;
Raithby, Paul R. ;
Warren, John E. ;
GleaveO, Robert .
ORGANIC LETTERS, 2007, 9 (11) :2119-2122
[10]   Enantioselective protonation of the lithium transient enolate of 2-methyltetralone with 2-sulfinyl alcohols [J].
Gil, J ;
Medio-Simon, M ;
Mancha, G ;
Asensio, G .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (08) :1561-1567