Reductive Generation of Aldehyde Metal Enolate from Ketene. A One-Flask Process to 1,1,2-and 1,2,2-Trisubstituted Dihydronaphthalenes from 1- and 2-Naphthalenecarboxylates

Kiyoshi Tomioka, Mitsuru Shindo, Kenji Koga

Research output: Contribution to journalArticle

38 Citations (Scopus)

Abstract

Successive treatment of 2,6-di-fert-buty1-4-(methoxypheny1)-1- and -2-naphthalenecarboxylates (BHAesters) (1, 2) with organolithium in THE, lithium triethylborohydride in refluxing THE, methyl iodide-HMPA, and finally sodium borohydride in MeOH provided regioand stereoselectively 1,1,2- and 1,2,2-trisubstituted dihydronaphthalenes (3, 4), respectively, in good yields. This one-flask process is constituted from a sequence of five reactions involving reductive generation of aldehyde metal enolate from ketene as a key step.

Original languageEnglish
Pages (from-to)2276-2277
Number of pages2
JournalJournal of Organic Chemistry
Volume55
Issue number8
DOIs
Publication statusPublished - Jan 1 1990
Externally publishedYes

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Hempa
Lithium
Aldehydes
Metals
sodium borohydride
ketene
methyl iodide

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

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title = "Reductive Generation of Aldehyde Metal Enolate from Ketene. A One-Flask Process to 1,1,2-and 1,2,2-Trisubstituted Dihydronaphthalenes from 1- and 2-Naphthalenecarboxylates",
abstract = "Successive treatment of 2,6-di-fert-buty1-4-(methoxypheny1)-1- and -2-naphthalenecarboxylates (BHAesters) (1, 2) with organolithium in THE, lithium triethylborohydride in refluxing THE, methyl iodide-HMPA, and finally sodium borohydride in MeOH provided regioand stereoselectively 1,1,2- and 1,2,2-trisubstituted dihydronaphthalenes (3, 4), respectively, in good yields. This one-flask process is constituted from a sequence of five reactions involving reductive generation of aldehyde metal enolate from ketene as a key step.",
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T1 - Reductive Generation of Aldehyde Metal Enolate from Ketene. A One-Flask Process to 1,1,2-and 1,2,2-Trisubstituted Dihydronaphthalenes from 1- and 2-Naphthalenecarboxylates

AU - Tomioka, Kiyoshi

AU - Shindo, Mitsuru

AU - Koga, Kenji

PY - 1990/1/1

Y1 - 1990/1/1

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AB - Successive treatment of 2,6-di-fert-buty1-4-(methoxypheny1)-1- and -2-naphthalenecarboxylates (BHAesters) (1, 2) with organolithium in THE, lithium triethylborohydride in refluxing THE, methyl iodide-HMPA, and finally sodium borohydride in MeOH provided regioand stereoselectively 1,1,2- and 1,2,2-trisubstituted dihydronaphthalenes (3, 4), respectively, in good yields. This one-flask process is constituted from a sequence of five reactions involving reductive generation of aldehyde metal enolate from ketene as a key step.

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