Gated access to α-lithiated phenyltetrahydrofuran: functionalisation via direct lithiation of the parent oxygen heterocycle.
Cycloreversion of α-lithiated phenyltetrahydrofuran was successfully tamed at -78 °C in a non-coordinating solvent in the presence of TMEDA. This anion showed excellent nucleophilicity and could be intercepted with a variety of structurally different electrophiles to give 2,2-disubstituted derivatives which can be further elaborated to γ-butyrolactones.
Dipartimento di Farmacia - Scienze del Farmaco, Università di Bari "Aldo Moro", Consorzio C.I.N.M.P.I.S, via E. Orabona 4, I-70125 Bari, Italy. vito.capriati@uniba.it.
Rosmara
R
Mansueto
Valentina
V
Mallardo
Filippo Maria
FM
Perna
Antonio
A
Salomone
Vito
V
Capriati
D015107:4-Butyrolactone / Q000737:chemistry; D003080:Cold Temperature; D005663:Furans / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*
D005663:Furans; D006571:Heterocyclic Compounds; C018674:tetrahydrofuran; D008094:Lithium; D015107:4-Butyrolactone; D010100:Oxygen