3,3-Diethoxypropyl-lithium: a masked lithium propanal homoenolate in organic synthesis

Abstract

3,3-Diethoxypropyl-lithium is prepared by lithiation of the corresponding chlorinated precursor with lithium naphthalenide at –78 °C; the reaction of this masked propanal homoenolate with different electrophilic reagents [H₂O, D₂O, (PhCH₂)₂S₂, PrCHO, BuⁱCHO, PhCHO, n-C₇H₁₅CHO, PhCHCHCHO, [[graphic omitted]O, [[graphic omitted]O, PhCOMe, PhCHNPh, PhCONEt₂, PhCN, c-C₆H₄CN, 4-MeC₆H₄CN] leads to the corresponding mono- and bi-functionalized compounds. In the case of the reaction with aldehydes or ketones the prepared crude products are oxidized with m-chloroperbenzoic acid, yielding directly the γ-substituted butyrolactones.