1,3-dipolar cycloadditions. Part XII - selective cycloaddition route to 4-nitroisoxazolidine ring systems

2007 ◽  
Vol 44 (5) ◽  
pp. 1045-1049 ◽  
Author(s):  
Avijit Banerji ◽  
Maya Gupta ◽  
Pizush Kanti Biswas ◽  
Thierry Prangé ◽  
Alain Neuman
Keyword(s):  
Ring Systems ◽  
Dipolar Cycloadditions

Use of highly stereospecific 1,3-dipolar cycloadditions of cyclic nitrones with acetylenes in the preparation of novel heterocyclic ring systems

1997 ◽  
pp. 155-162 ◽  
Author(s):  
W. Russell Bowman ◽  
Roy V. Davies ◽  
Alexandra M. Z. Slawin ◽  
Gian S. Sohal ◽  
Roger B. Titman ◽  
...  
Keyword(s):  
Heterocyclic Ring ◽  
Ring Systems ◽  
Dipolar Cycloadditions ◽  
Cyclic Nitrones

Intramolecular 1,4-Dipolar Cycloadditions of Cross-Conjugated Heteroaromatic Betaines. Synthesis of Hexahydrojulolidines and Related Peri- and Ortho-Fused Ring Systems

1995 ◽  
Vol 60 (12) ◽  
pp. 3795-3805 ◽  
Author(s):  
Kevin T. Potts ◽  
Thevarak Rochanapruk ◽  
Albert Padwa ◽  
Steven J. Coats ◽  
Lazaros Hadjiarapoglou
Keyword(s):  
Ring Systems ◽  
Dipolar Cycloadditions ◽  
Fused Ring

scholarly journals Facile generation of bridged medium-sized polycyclic systems by rhodium-catalysed intramolecular (3+2) dipolar cycloadditions

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Bao-Long Hou ◽  
Jonathan J. Wong ◽  
Na Lv ◽  
Yong-Qiang Wang ◽  
K. N. Houk ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Single Step ◽  
Bioactive Molecules ◽  
Dipolar Cycloaddition ◽  
General Strategy ◽  
Diastereoselective Synthesis ◽  
Asymmetric Total Synthesis ◽  
Ring Systems ◽  
Dipolar Cycloadditions ◽  
Unusual Type

AbstractBridged medium-sized bicyclo[m.n.2] ring systems are common in natural products and potent pharmaceuticals, and pose a great synthetic challenge. Chemistry for making bicyclo[m.n.2] ring systems remains underdeveloped. Currently, there are no general reactions available for the single-step synthesis of various bridged bicyclo[m.n.2] ring systems from acyclic precursors. Here, we report an unusual type II intramolecular (3+2) dipolar cycloaddition strategy for the syntheses of various bridged bicyclo[m.n.2] ring systems. This rhodium-catalysed cascade reaction provides a relatively general strategy for the direct and efficient regioselective and diastereoselective synthesis of highly functionalized and synthetically challenging bridged medium-sized polycyclic systems. Asymmetric total synthesis of nakafuran-8 was accomplished using this method as a key step. Quantum mechanical calculations demonstrate the mechanism of this transformation and the origins of its multiple selectivities. This reaction will inspire the design of the strategies to make complex bioactive molecules with bridged medium-sized polycyclic systems.

ChemInform Abstract: Use of Highly Stereospecific 1,3-Dipolar Cycloadditions of Cyclic Nitrones with Acetylenes in the Preparation of Novel Heterocyclic Ring Systems.

ChemInform ◽  
2010 ◽  
Vol 28 (31) ◽  
pp. no-no
Author(s):  
W. R. BOWMAN ◽  
R. V. DAVIES ◽  
A. M. Z. SLAWIN ◽  
G. S. SOHAL ◽  
R. B. TITMAN ◽  
...  
Keyword(s):  
Heterocyclic Ring ◽  
Ring Systems ◽  
Dipolar Cycloadditions ◽  
Cyclic Nitrones

ChemInform Abstract: 1,3-Dipolar Cycloadditions. Part 12. Selective Cycloaddition Route to 4-Nitroisoxazolidine Ring Systems.

ChemInform ◽  
2008 ◽  
Vol 39 (4) ◽  
Author(s):  
Avijit Banerji ◽  
Maya Gupta ◽  
Pizush Kanti Biswas ◽  
Thierry Prange ◽  
Alain Neuman
Keyword(s):  
Ring Systems ◽  
Dipolar Cycloadditions
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