Design, synthesis, and reactivity of 1-hydrazinodienes for use in organic synthesis.
A new 1-hydrazinodiene (1) has been developed and utilized in Lewis acid catalyzed, intermolecular Diels-Alder reactions with various electron-deficient alkenes. The hydrazine can then be deprotected, and a molecule of methanesulfinic acid is eliminated to provide a putative diazene intermediate (4), which then spontaneously undergoes a suprafacial 1,5-sigmatropic shift to yield stereochemically complex cyclohexenes. This method has been applied to the synthesis of a constitutionally and stereochemically complex decalin derivative.
Sammis
Glenn M
GM
Department of Chemistry, Princeton University, Princeton, New Jersey 08544-1009, USA.
Flamme
Eric M
EM
Xie
Hao
H
Ho
Douglas M
DM
Sorensen
Erik J
EJ
D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D002625:Chemistry, Organic / Q000379:methods; D003500:Cyclization; D006834:Hydrazines / Q000138:chemical synthesis / Q000737:chemistry*
D000475:Alkenes; D006834:Hydrazines