The first method for protection-deprotection of the indole 2,3-pi bond.
[reaction: see text] The scope and generality of a new reaction of indoles with MTAD is discussed. In most cases the ene-type reaction proceeds within seconds or minutes at 0 degrees C to provide the urazole adducts in high yield. This reaction provides the first method for protecting the indole 2,3-double bond since the urazole adducts can be reconverted to the starting indole (retro-ene) simply by heating.
Baran
Phil S
PS
Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
Guerrero
Carlos A
CA
Corey
E J
EJ
D018360:Crystallography, X-Ray; D007202:Indicators and Reagents; D007211:Indoles / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism; D014230:Triazoles / Q000737:chemistry*
D007202:Indicators and Reagents; D007211:Indoles; D014230:Triazoles; C068159:4-methyl-1,2,4-triazoline-3,5-dione