Caveat in the stereochemical outcome of the organocatalytic Diels-Alder reaction in PEG-400

被引:3
作者
Anitha, Pantapalli M. [1 ]
Mainkar, Prathama S. [1 ]
Kallepu, Shivakrishna [1 ]
Babu, V. S. Phani [2 ]
Reddy, Cirandur Suresh [3 ]
Chandrasekhar, Srivari [1 ]
机构
[1] Indian Inst Chem Technol, CSIR, Div Nat Prod Chem, Hyderabad 500007, Andhra Pradesh, India
[2] Indian Inst Chem Technol, CSIR, Ctr NMR & Struct Chem, Hyderabad 500007, Andhra Pradesh, India
[3] Sri Venkateswara Univ, Dept Chem, Tirupati, Andhra Pradesh, India
关键词
Positive ions;
D O I
10.1039/c6ra15035g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The organocatalytic Diels-Alder reaction in non-conventional solvent (PEG-400) has yielded cycloaddition products with diaster-eoselectivities hitherto not reported in detail using classical reaction conditions.
引用
收藏
页码:76132 / 76136
页数:5
相关论文
共 50 条
[1]   New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction [J].
Ahrendt, KA ;
Borths, CJ ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) :4243-4244
[2]   Advanced Strategies for Efficient Macrocyclic Cu(I)-Catalyzed Cycloaddition of Azides [J].
Bedard, Anne-Catherine ;
Collins, Shawn K. .
ORGANIC LETTERS, 2014, 16 (20) :5286-5289
[3]   Continuous flow macrocyclization at high concentrations: synthesis of macrocyclic lipids [J].
Bedard, Anne-Catherine ;
Regnier, Sophie ;
Collins, Shawn K. .
GREEN CHEMISTRY, 2013, 15 (07) :1962-1966
[4]   Exploiting Aggregation To Achieve Phase Separation in Macrocyclization [J].
Bedard, Anne-Catherine ;
Collins, Shawn K. .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (06) :2108-2113
[5]   Phase Separation As a Strategy Toward Controlling Dilution Effects in Macrocyclic Glaser-Hay Couplings [J].
Bedard, Anne-Catherine ;
Collins, Shawn K. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (49) :19976-19981
[6]   The α-effect in iminium ion catalysis [J].
Cavill, JL ;
Elliott, RL ;
Evans, G ;
Jones, IL ;
Platts, JA ;
Ruda, AM ;
Tomkinson, NCO .
TETRAHEDRON, 2006, 62 (2-3) :410-421
[7]   Copper-catalyzed N-arylation of amines/amides in poly(ethylene glycol) as recyclable solvent medium [J].
Chandrasekhar, S ;
Sultana, SS ;
Yaragorla, SR ;
Reddy, NR .
SYNTHESIS-STUTTGART, 2006, (05) :839-842
[8]   Poly(ethylene glycol) (400) as superior solvent medium against ionic liquids for catalytic hydrogenations with PtO2 [J].
Chandrasekhar, S ;
Prakash, SJ ;
Rao, CL .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (05) :2196-2199
[9]   L-Proline catalysed asymmetric aldol reactions in PEG-400 as recyclable medium and transfer aldol reactions [J].
Chandrasekhar, S ;
Reddy, NR ;
Sultana, SS ;
Narsihmulu, C ;
Reddy, KV .
TETRAHEDRON, 2006, 62 (2-3) :338-345
[10]   Pd/CaCO3 in liquid poly(ethylene glycol) (PEG):: an easy and efficient recycle system for partial reduction of alkynes to cis-olefins under a hydrogen atmosphere [J].
Chandrasekhar, S ;
Narsihmulu, C ;
Chandrashekar, G ;
Shyamsunder, T .
TETRAHEDRON LETTERS, 2004, 45 (11) :2421-2423