RETRACTED: Enantioselective Organocatalytic Hantzsch Synthesis of Polyhydroquinolines (Retracted article. See vol. 23, pg. 3802, 2021)

被引：127
作者：
Evans, Christopher G.
Gestwicki, Jason E. [1 ]
机构：
[1] Univ Michigan, Dept Pathol, Ann Arbor, MI 48109 USA
来源：
ORGANIC LETTERS | 2009年 / 11卷 / 14期
关键词：
ONE-POT SYNTHESIS; MICROWAVE-ASSISTED SYNTHESIS; EFFICIENT ONE-POT; MULTICOMPONENT REACTIONS; TRANSFER HYDROGENATION; 3-COMPONENT SYNTHESIS; BIGINELLI REACTION; MANNICH REACTIONS; DERIVATIVES; GENERATION;
D O I：
10.1021/ol901114f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The four-component Hantzsch reaction provides access to pharmaceutically important dihydropyridines. To expand the utility of this method, we have developed a route under organocatalytic conditions with good yields and excellent ee's. Through catalyst screening, we found that a BINOL-phosphoric acid allowed enantioselective synthesis of six-membered heterocycles with a variety of substitution patterns.
引用
收藏
页码：2957 / 2959
页数：3
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共 48 条
[1]   Stereochemical control of the Passerini reaction [J].
Andreana, PR ;
Liu, CC ;
Schreiber, SL .
ORGANIC LETTERS, 2004, 6 (23) :4231-4233
[2]   Microwave-assisted three-component synthesis of 7-aryl-2-alkylthio-4,7-dihydro-1,2,4-triazolo[1,5-a]-pyrimidine-6-carboxamides and their selective reduction [J].
Chebanov, VA ;
Muravyova, EA ;
Desenko, SM ;
Musatov, VI ;
Knyazeva, IV ;
Shishkina, SV ;
Shishkin, OV ;
Kappe, CO .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2006, 8 (03) :427-434
[3]   One-pot, multicomponent route to pyrazoloquinolizinones [J].
Chebanov, Valentin A. ;
Saraev, Vyacheslav E. ;
Desenko, Sergey M. ;
Chemenko, Vitaliy N. ;
Shishkina, Svetlana V. ;
Shishkin, Oleg V. ;
Kobzar, Kiril M. ;
Kappe, C. Oliver .
ORGANIC LETTERS, 2007, 9 (09) :1691-1694
[4]   Highly enantioselective organocatalytic Biginelli reaction [J].
Chen, Xiao-Hua ;
Xu, Xiao-Ying ;
Liu, Hua ;
Cun, Lin-Feng ;
Gong, Liu-Zhu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (46) :14802-14803
[5]   P-TSA catalyzed facile and efficient synthesis of polyhydroquinoline derivatives through Hantzsch multi-component condensation [J].
Cherkupally, Sanjeeva Reddy ;
Mekala, Raghu .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2008, 56 (07) :1002-1004
[6]   Automated generation of a dihydropyrimidine compound library using microwave-assisted processing [J].
Dallinger, Doris ;
Kappe, C. Oliver .
NATURE PROTOCOLS, 2007, 2 (07) :1713-1721
[7]   An efficient one-pot synthesis of polyhydroquinolines at room temperature using HY-Zeolite [J].
Das, Biswanath ;
Ravikanth, Bommena ;
Ramu, Ravirala ;
Rao, Bommena Vittal .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2006, 54 (07) :1044-1045
[8]   A Tandem One-Pot, Microwave-Assisted Synthesis of Regiochemically Differentiated 1,2,4,5-Tetrahydro-1 4-benzodiazepin-3-ones [J].
De Silva, Ravindra A. ;
Santra, Soumava ;
Andreana, Peter R. .
ORGANIC LETTERS, 2008, 10 (20) :4541-4544
[9]   Three-component Biginelli cyclocondensation reaction using C-glycosylated substrates.: Preparation of a collection of dihydropyrimidinone glycoconjugates and the synthesis of C-glycosylated monastrol analogues [J].
Dondoni, A ;
Massi, A ;
Sabbatini, S ;
Bertolasi, V .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) :6979-6994
[10]   Hantzsch-type three-component approach to a new family of carbon-linked glycosyl amino acids. synthesis of C-glycosylmethyl pyridylalanines [J].
Dondoni, Alessandro ;
Massi, Alessandro ;
Aldhoun, Mohammad .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (20) :7677-7687
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