Zinc-copper(I) chloride or -silver acetate promoted coupling reaction of 2-[(Trimethylsilyl)methyl]-3-chloro-3,3-difluoropropene with carbonyl compounds. Highly efficient access to 2,2-difluoro homoallyl alcohols

Takashi Ishihara, Seiji Miwatashi, Manabu Kuroboshi, Kiitiro Utimoto

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

2-[(Trimethylsilyl)methyl]-3-chloro-3,3-difluoropropene, readily prepared in two steps from methyl chlorodifluoroacetate and (trimethylsilyl)methylmagnesium chloride, is reduced to couple regioselectivity with a variety of carbonyl compounds in the presence of zinc-copper(I) chloride or -silver acetate to give 2,2-difluoro-3-[(trimethylsilyl)methyl]-3-buten-1-ol derivatives in good to excellent yields.

Original languageEnglish
Pages (from-to)1069-1072
Number of pages4
JournalTetrahedron Letters
Volume32
Issue number8
DOIs
Publication statusPublished - Feb 18 1991
Externally publishedYes

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Carbonyl compounds
Regioselectivity
Zinc
Chlorides
Alcohols
Derivatives
3,3-difluoropropene
cuprous chloride
silver acetate
3-methyl-3-buten-1-ol
trimethylsilyl chloride

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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title = "Zinc-copper(I) chloride or -silver acetate promoted coupling reaction of 2-[(Trimethylsilyl)methyl]-3-chloro-3,3-difluoropropene with carbonyl compounds. Highly efficient access to 2,2-difluoro homoallyl alcohols",
abstract = "2-[(Trimethylsilyl)methyl]-3-chloro-3,3-difluoropropene, readily prepared in two steps from methyl chlorodifluoroacetate and (trimethylsilyl)methylmagnesium chloride, is reduced to couple regioselectivity with a variety of carbonyl compounds in the presence of zinc-copper(I) chloride or -silver acetate to give 2,2-difluoro-3-[(trimethylsilyl)methyl]-3-buten-1-ol derivatives in good to excellent yields.",
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T1 - Zinc-copper(I) chloride or -silver acetate promoted coupling reaction of 2-[(Trimethylsilyl)methyl]-3-chloro-3,3-difluoropropene with carbonyl compounds. Highly efficient access to 2,2-difluoro homoallyl alcohols

AU - Ishihara, Takashi

AU - Miwatashi, Seiji

AU - Kuroboshi, Manabu

AU - Utimoto, Kiitiro

PY - 1991/2/18

Y1 - 1991/2/18

N2 - 2-[(Trimethylsilyl)methyl]-3-chloro-3,3-difluoropropene, readily prepared in two steps from methyl chlorodifluoroacetate and (trimethylsilyl)methylmagnesium chloride, is reduced to couple regioselectivity with a variety of carbonyl compounds in the presence of zinc-copper(I) chloride or -silver acetate to give 2,2-difluoro-3-[(trimethylsilyl)methyl]-3-buten-1-ol derivatives in good to excellent yields.

AB - 2-[(Trimethylsilyl)methyl]-3-chloro-3,3-difluoropropene, readily prepared in two steps from methyl chlorodifluoroacetate and (trimethylsilyl)methylmagnesium chloride, is reduced to couple regioselectivity with a variety of carbonyl compounds in the presence of zinc-copper(I) chloride or -silver acetate to give 2,2-difluoro-3-[(trimethylsilyl)methyl]-3-buten-1-ol derivatives in good to excellent yields.

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