129633-63-2Relevant academic research and scientific papers
A one-flask synthesis of dihydronaphthalenemethanols by directed addition of organolithium reagents to BHA naphthalenecarboxylates
Shindo, Mitsuru,Koga, Kenji,Asano, Yasutomi,Tomioka, Kiyoshi
, p. 4955 - 4968 (1999)
The 1,4-addition reaction of organolithium reagents with 2,6-bis(tert- butyl)-4-methoxyphenyl naphthalenecarboxylates gave regioselectively substituted dihydronaphthalenecarboxylates in high yields. Successive treatment of the esters with organolithiums in THF, lithium triethylborohydride, methyl iodide, and finally sodium borohydride in methanol, provided vegio- and stereoselectively the corresponding 1,1,2- and 1,2,2-trisubstituted dihydronaphthalenylmethanols in good yields. This one- flask process is constituted from a sequence of five reactions involving a reductive generation of an aldehyde metal enolate from a ketene as the key step.
