1,3-dipolar cycloaddition on solid supports:: nitrone approach towards isoxazolidines and isoxazolines and subsequent transformations

被引:170
作者
Rück-Braun, K [1 ]
Freysoldt, THE [1 ]
Wierschem, F [1 ]
机构
[1] Tech Univ Berlin, Inst Chem, D-10623 Berlin, Germany
关键词
D O I
10.1039/b311200b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
1,3-Dipolar cycloaddition reactions of nitrones with alkenes and alkynes are well-studied reactions in solution-phase organic chemistry. However, the number of studies concerned with their application in solid-phase organic synthesis is rather low compared to other 1,3-dipoles, e.g. azides or nitrile oxides. This tutorial review aims to summarise the main approaches towards the application of nitrones in 1,3-dipolar cycloaddition reactions on solid supports in addition to subsequent transformations with polymer-bound isoxazolidines and reactions using polymer-bound catalysts.
引用
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页码:507 / 516
页数:10
相关论文
共 36 条
[1]   Recent advances in asymmetric C-C and C-heteroatom bond forming reactions using polymer-bound catalysts [J].
Bräse, S ;
Lauterwasser, F ;
Ziegert, RE .
ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (08) :869-929
[2]   A soluble polymer-bound Evans' chiral auxiliary: synthesis, characterization and use in cycloaddition reactions [J].
Desimoni, G ;
Faita, G ;
Galbiati, A ;
Pasini, D ;
Quadrelli, P ;
Rancati, F .
TETRAHEDRON-ASYMMETRY, 2002, 13 (04) :333-337
[3]   Comprehensive survey of combinatorial library synthesis: 2003 [J].
Dolle, RE .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2004, 6 (05) :623-679
[4]   (4S)-p-hydroxybenzyl-1,3-oxazolidin-2-one as a solid-supported chiral auxiliary in asymmetric 1,3-dipolar cycloadditions [J].
Faita, G ;
Paio, A ;
Quadrelli, P ;
Rancati, F ;
Seneci, P .
TETRAHEDRON LETTERS, 2000, 41 (08) :1265-1269
[5]   Solid supported chiral auxiliaries in asymmetric synthesis. Part 2: Catalysis of 1,3-dipolar cycloadditions by Mg(II) cation [J].
Faita, G ;
Paio, A ;
Quadrelli, P ;
Rancati, F ;
Seneci, P .
TETRAHEDRON, 2001, 57 (39) :8313-8322
[6]   Asymmetric 1,3-dipolar cycloaddition reactions [J].
Gothelf, KV ;
Jorgensen, KA .
CHEMICAL REVIEWS, 1998, 98 (02) :863-909
[7]   Solid phase synthesis of diverse isoxazolidines via 1,3-dipolar cycloaddition [J].
Haap, WJ ;
Kaiser, D ;
Walk, TB ;
Jung, G .
TETRAHEDRON, 1998, 54 (15) :3705-3724
[8]  
Heckel A, 2002, CHEM-EUR J, V8, P559, DOI 10.1002/1521-3765(20020201)8:3<559::AID-CHEM559>3.3.CO
[9]  
2-T
[10]  
Heckel A, 2000, ANGEW CHEM INT EDIT, V39, P163, DOI 10.1002/(SICI)1521-3773(20000103)39:1<163::AID-ANIE163>3.0.CO