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

Mitsuru Shindo, Kenji Koga, Yasutomi Asano, Kiyoshi Tomioka

研究成果: Contribution to journalArticle査読

33 被引用数 (Scopus)

抄録

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.

本文言語英語
ページ(範囲)4955-4968
ページ数14
ジャーナルTetrahedron
55
16
DOI
出版ステータス出版済み - 4 16 1999
外部発表はい

All Science Journal Classification (ASJC) codes

  • 生化学
  • 創薬
  • 有機化学

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