Dearomatizing anionic cyclizations of N-benzyl-N-methyldiphenylphosphinamides. Synthesis of gamma-(N-methylamino)phosphinic acids.
The first dearomatizing anionic reaction of a phenyl ring promoted by an N-benzyl-N-methylphosphinamide group is described. The intermediate lithium species can be trapped with different electrophiles, affording tetrahydrobenzo[c]-1-aza-2lambda(5)-phospholes with excellent diastereoselectivity. The new process is a simple and very efficient entry to the stereoselective synthesis of functionalized gamma-(N-methylamino)phosphinic acids and esters.
Fernández
I
I
Area de Química Orgánica, Universidad de Almería, Carretera de Sacramento s/n, 04120 Almería, Spain.
Ortiz
F L
FL
Tejerina
B
B
Granda
S G
SG