156300-84-4Relevant academic research and scientific papers
Directed Ortho Metalations of Tertiary Benzamides Using Lactones as Electrophiles
Brenstrum, Timothy J.,Brimble, Margaret A.,Stevenson, Ralph J.
, p. 4897 - 4904 (1994)
Directed ortho metalation of oxygenated tertiary benzamides using tert-butyllithium in THF/TMEDA at -78 deg C followed by the addition of a range of lactones afforded ortho-substituted keto-alcohols in good yield.
Synthesis of aromatic spiroacetals
Brimble, Margaret A.,Horner, Gillian M.,Stevenson, Ralph J.
, p. 189 - 196 (2007/10/03)
The synthesis of aromatic spiroacetal ring systems related to the papulacandins is reported. ortho-Metalation of diisopropylbenzamide, followed by reaction with the electrophiles δ-valerolactone. γ-butyrolactone and γ-valerolactone, provided the keto alcohol adducts (10), (16) and (21) respectively. Reduction of the ketone followed by treatment with acid afforded phthalides (12), (18) and (23). Finally oxidative cyclization with iodobenzene diacetate provided the spiroacetals (7), (14) and (19).
