A one-flask synthesis of dihydronaphthalenemethanols by directed addition of organolithium reagents to BHA naphthalenecarboxylates

✍ Scribed by Mitsuru Shindo; Kenji Koga; Yasutomi Asano; Kiyoshi Tomioka

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 948 KB
• Volume: 55
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(99)00181-7

✦ Synopsis

The 1,44addition reaction of organolithium reagentS with 2,6-bis(tert-butyl)-44methoxyphenyl naphthalenecarboxylates gave regioselectively substituted dihydronaphthalenecarboxylates in high yields. Successive treatment of the esters with organofithiums in THF, lithium triethylborohyda4de, methyl iodide, and finally sodium borohydride in methanol, provided regio-and stereoselecfively the corresponding 1,I,2-and 1,2,2-trisubstituted dihydronaphthalenylmethanols in good yields. This oneflask 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.