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

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 io...

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Bibliographic Details
Published in:Tetrahedron 1999-04, Vol.55 (16), p.4955-4968
Main Authors: Shindo, Mitsuru, Koga, Kenji, Asano, Yasutomi, Tomioka, Kiyoshi
Format: Article
Language:English
Subjects:
Addition reactions
Esters
Ketene
Naphthalenes
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Summary: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 regio- 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. One-pot reaction of BHA naphthalenecarboxylates with organolithium reagents gave dihydronaphthalenemethanol.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(99)00181-7