3-Indolyl-,(N-methyl-3-indolyl)-, and (N-methyl-2-methyl-3-indolyl) acetic acids are quantitatively a-lithiated directly with n-BuLi, while methyl (N-methyl-34ndolyl) acetate is quantitatively a-lithiated with lithium diisopropylarnide (LDA) at-78" C in THF. These useful synthons react readily with electrophiles such as alkyl halides, chlorosilanes, and ketones to afford the respective a-alkyl derivatives 1, ketene silyl acetals 2, and@-hydroxy acids 3. ...
