C. A. Bayse, B. K. Carpenter, J. Wilmot
Jan 1, 2002
Citations
0
Influential Citations
1
Citations
Journal
Synthetic Communications
Abstract
ABSTRACT The reductive dialkylation of diethyl 1,4-naphthalenedicarboxylate is achieved in high yield and moderate diastereoselectivity. In liquid ammonia at −78°C, a 5.6 : 1 ratio of trans- to cis-1,4-dimethyl-1,4-naphthalenedicarboxylates is obtained. The reductive dialkylation can also be carried out under more convenient conditions in THF at room temperature with no loss in yield, but a two-fold loss in diastereoselectivity. The alternate method is also used to synthesize 1,4-dialkylated products from ethyl bromide and allyl bromide.