5. Ester enolates (as well as enolates from ketones) are often best generated using sterically hindered...
5. Ester enolates (as well as enolates from ketones) are often best generated using sterically hindered bases such as t-butoxide, since a bulky base will be less likely to act as a nucleophile and attack the carbonyl carbon. Give the enolates generated by the following bulky bases, then show the product of enolate alkylation. (Hint – the second step is an SN2 reaction.). The first one is done as an example. Be sure to count your carbons! Br + LIEN Eto EIO THF Eto LDA & CI Ph + TMS, NK THE Eto CH3 + LDA RO THF 2