INTRAMOLECULAR CATIONIC [5 + 2] CYCLOADDITION REACTIONS PROMOTED BY TRIMETHYLSILYL TRIFLATE IN 3.0 M LITHIUM PERCHLORATE-ETHYL ACETATE: APPLICATION TO A FORMAL TOTAL SYNTHESIS OF (±)-ISOCOMENE

Tetrahedron ◽  
1997 ◽  
Vol 53 (26) ◽  
pp. 8975-8996
Author(s):  
P Grieco*
Keyword(s):  
Total Synthesis ◽  
Ethyl Acetate ◽  
Lithium Perchlorate ◽  
Cycloaddition Reactions

Aziridinyl imines in organic synthesis: Development of tandem reaction strategies and application to total synthesis of natural products

2013 ◽  
Vol 85 (4) ◽  
pp. 741-753 ◽  
Author(s):  
Hee-Yoon Lee ◽  
Seog-Beom Song ◽  
Taek Kang ◽  
Yoon Jung Kim ◽  
Su Jeong Geum
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Organic Synthesis ◽  
Reactive Intermediates ◽  
Diazo Compounds ◽  
Tandem Reaction ◽  
Cycloaddition Reactions ◽  
Free Radical Reactions ◽  
Sulfur Ylide ◽  
Epoxide Formation

Aziridinyl imines are well-known carbene equivalents because they are precursors of diazo compounds from which reactive intermediates can be produced. These carbene equivalents can be utilized as zwitterionic species, diradicals, or 4π system for cycloaddition reactions. Thus, the intermediates derived from aziridinyl imines have been used in the sulfur-ylide-mediated epoxide formation, tandem free-radical reactions, or cyclopropanation reaction via carbene intermediates to form trimethylenemethane (TMM) diyls, which undergo [2 + 3] cycloaddition reactions to form cyclopentanoids. Diazo compounds generated from aziridinyl imines also react with allenes to form TMM diyls. This reaction was utilized in tandem cycloaddition reactions of linear substrates to form polyquinanes. These tandem reaction strategies were successfully applied to the total synthesis of various cyclopentanoid natural products.

The nature of lithium perchlorate and gallium chloride salt effect in cycloaddition reactions

Tetrahedron ◽  
1998 ◽  
Vol 54 (11) ◽  
pp. 2631-2646 ◽  
Author(s):  
Yury G. Shtyrlin ◽  
Dmitry G. Murzin ◽  
Natalia A. Luzanova ◽  
Gulnara G. Iskhakova ◽  
Vladimir D. Kiselev ◽  
...  
Keyword(s):  
Salt Effect ◽  
Lithium Perchlorate ◽  
Chloride Salt ◽  
Cycloaddition Reactions ◽  
Gallium Chloride
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