A Novel Diastereoselective Multicomponent Cascade Reaction

被引:50
作者
Kriis, Kadri [1 ]
Ausmees, Kerti [1 ]
Pehk, Tonis [2 ]
Lopp, Margus [1 ]
Kanger, Tonis [1 ]
机构
[1] Tallinn Univ Technol, Dept Chem, EE-12618 Tallinn, Estonia
[2] NICPB, EE-12618 Tallinn, Estonia
关键词
STEREOSELECTIVE-SYNTHESIS; MICHAEL ADDITION; DOMINO REACTIONS; ORGANOCATALYSTS; ISONITRILE;
D O I
10.1021/ol1005714
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel multicomponent cascade reaction led to the formation of a strained 3-azabicyclo[3.2.0]heptane derivative 4. The unstable ester 4 was reduced in a one-pot procedure to a stable alcohol 6. The formation of the bicyclic product is highly diastereoselective, predominantly affording one diastereoisomer. The obtained azabicycloheptanes are important pharmacophores.
引用
收藏
页码:2230 / 2233
页数:4
相关论文
共 31 条
[1]   Facial diastereoselectivity in the [2+2]-photocycloaddition of chiral vinylglycine-derived N,N-diallyl amines [J].
Bach, T ;
Pelkmann, C ;
Harms, K .
TETRAHEDRON LETTERS, 1999, 40 (11) :2103-2104
[2]  
Bach T, 2000, SYNTHESIS-STUTTGART, P305
[3]   Iron-catalyzed [2π+2π] cycloaddition of α,ω-dienes:: The importance of redox-active supporting ligands [J].
Bouwkamp, Marco W. ;
Bowman, Amanda C. ;
Lobkovsky, Emil ;
Chirik, Paul J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (41) :13340-13341
[4]   Enantioselective organocatalytic amine conjugate addition [J].
Chen, Young K. ;
Yoshida, Masanori ;
MacMillan, David W. C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (29) :9328-9329
[5]   Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].
Dömling, A .
CHEMICAL REVIEWS, 2006, 106 (01) :17-89
[6]  
Drescher K., 2006, PCT Int. Appl. WO, Patent No. 2006040176
[7]   Lessons from nature: Biomimetic organocatalytic carbon-carbon bond formations [J].
Enders, Dieter ;
Narine, Arun A. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (20) :7857-7870
[8]   Asymmetric organocatalytic domino reactions [J].
Enders, Dieter ;
Grondal, Christoph ;
Huettl, Matthias R. M. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) :1570-1581
[9]   Organocatalytic Asymmetric Aza-Michael Additions [J].
Enders, Dieter ;
Wang, Chuan ;
Liebich, Jens X. .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (42) :11058-11076
[10]   Iminium catalysis [J].
Erkkila, Anniina ;
Majander, Inkeri ;
Pihko, Petri M. .
CHEMICAL REVIEWS, 2007, 107 (12) :5416-5470