Room-temperature reductive dialkylation of diethyl naphthalenedicarboxylate
Document Type
Article
Publication Date
1-1-2002
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.
Publication Title
Synthetic Communications
Recommended Citation
Bayse, C.,
Carpenter, B.,
&
Wilmot, J.
(2002).
Room-temperature reductive dialkylation of diethyl naphthalenedicarboxylate.
Synthetic Communications,
32(17), 2705-2709.
http://doi.org/10.1081/SCC-120006036
Retrieved from: https://digitalcommons.mtu.edu/michigantech-p/9528