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

Mitsuru Shindo, Kenji Koga, Yasutomi Asano, Kiyoshi Tomioka

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31 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)4955-4968
Number of pages14
JournalTetrahedron
Volume55
Issue number16
DOIs
Publication statusPublished - Apr 16 1999
Externally publishedYes

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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