Highly enantioselective organocatalytic cascade reaction for the synthesis of piperidines and oxazolidines

被引：37
作者：
Cihalova, Sylva [2 ]
Valero, Guillem [1 ]
Schimer, Jiri [2 ]
Humpl, Marek [2 ]
Dracinsky, Martin [2 ]
Moyano, Albert [1 ]
Rios, Ramon [1 ,3 ]
Vesely, Jan [2 ]
机构：
[1] Univ Barcelona, Dept Organ Chem, E-08028 Barcelona, Spain
[2] Charles Univ Prague, Fac Sci, Dept Organ & Nucl Chem, Prague 12840, Czech Republic
[3] ICREA, Barcelona 08010, Spain
来源：
TETRAHEDRON | 2011年 / 67卷 / 46期
关键词：
Organocatalysis; Paroxetine; Enantioselective; Cascade reaction; Diastereoselective; DIELS-ALDER REACTION; ONE-POT; ALPHA; BETA-UNSATURATED ALDEHYDES; AZOMETHINE YLIDES; FORMAL SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; ATOM ECONOMY; 3-COMPONENT; CATALYSIS; (-)-PAROXETINE;
D O I：
10.1016/j.tet.2011.08.079
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of piperidines and piperidines derivatives in enantiopure fashion has been a challenging goal for organic chemists. In this report we developed a nice cascade reaction for piperidine derivatives based in an amidomalonate Michael addition to enals followed by an intramolecular hemiaminal formation with good yields and enantioselectivities. Moreover we studied the 'in situ' intramolecular cyclization of this hemiaminals with alcohols forming fused piperidine-oxazolidines. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：8942 / 8950
页数：9
相关论文
共 66 条
[1]   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
[2]   Formal Highly Enantioselective Organocatalytic Addition of Alkyl Anions to α,β-Unsaturated Aldehydes: Application to the Synthesis of Isotope-Enantiomers [J].
Alba, Andrea-Nekane ;
Companyo, Xavier ;
Moyano, Albert ;
Rios, Ramon .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (42) :11095-11099
[3]   Formal Highly Enantioselective Organocatalytic Addition of Fluoromethyl Anion to α,β-Unsaturated Aldehydes [J].
Alba, Andrea-Nekane ;
Companyo, Xavier ;
Moyano, Albert ;
Rios, Ramon .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (29) :7035-7038
[4]   Organocatalytic Domino Reactions [J].
Alba, Andrea-Nekane ;
Companyo, Xavier ;
Viciano, Monica ;
Rios, Ramon .
CURRENT ORGANIC CHEMISTRY, 2009, 13 (14) :1432-1474
[5]   Highly Stereoselective Synthesis of Spiropyrazolones [J].
Alba, Andrea-Nekane R. ;
Zea, Alex ;
Valero, Guillem ;
Calbet, Teresa ;
Font-Bardia, Merce ;
Mazzanti, Andrea ;
Moyano, Albert ;
Rios, Ramon .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (07) :1318-1325
[6]   Enantioselective Organocatalytic Addition of Azlactones to Maleimides: A Highly Stereocontrolled Entry to 2,2-Disubstituted-2H-oxazol-5-ones [J].
Alba, Andrea-Nekane R. ;
Valero, Guillem ;
Calbet, Teresa ;
Font-Bardia, Merce ;
Moyano, Albert ;
Rios, Ramon .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (32) :9884-9889
[7]   Sulfones: new reagents in organocatalysis [J].
Alba, Andrea-Nekane R. ;
Companyo, Xavier ;
Rios, Ramon .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (06) :2018-2033
[8]   Enantioselective Organocatalytic Addition of Oxazolones to 1,1-Bis(phenylsulfonyl)ethylene: A Convenient Asymmetric Synthesis of Quaternary α-Amino Acids [J].
Alba, Andrea-Nekane R. ;
Companyo, Xavier ;
Valero, Guillem ;
Moyano, Albert ;
Rios, Ramon .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (18) :5354-5361
[9]   Highly Regio- and Diastereoselective Oxazol-5-one Addition to Nitrostyrenes [J].
Balaguer, Andrea-Nekane ;
Companyo, Xavier ;
Calvet, Teresa ;
Font-Bardia, Merce ;
Moyano, Albert ;
Rios, Ramon .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (02) :199-203
[10]   Organocatalytic conjugate addition of malonates to α,β-unsaturated aldehydes:: Asymmetric formal synthesis of (-)-paroxetine, chiral lactams, and lactones [J].
Brandau, Sven ;
Landa, Aitor ;
Franzen, Johan ;
Marigo, Mauro ;
Jorgensen, Karl Anker .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (26) :4305-4309
1234567