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

doi:10.1016/S0040-4039(00)74490-X

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 journal › Article › peer-review

23 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 language	English
Pages (from-to)	1069-1072
Number of pages	4
Journal	Tetrahedron Letters
Volume	32
Issue number	8
DOIs	https://doi.org/10.1016/S0040-4039(00)74490-X
Publication status	Published - Feb 18 1991
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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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. / Ishihara, Takashi; Miwatashi, Seiji; Kuroboshi, Manabu et al.
In: Tetrahedron Letters, Vol. 32, No. 8, 18.02.1991, p. 1069-1072.

Research output: Contribution to journal › Article › peer-review

Ishihara, T, Miwatashi, S, Kuroboshi, M & Utimoto, K 1991, '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', Tetrahedron Letters, vol. 32, no. 8, pp. 1069-1072. https://doi.org/10.1016/S0040-4039(00)74490-X

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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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AU - Ishihara, Takashi

AU - Miwatashi, Seiji

AU - Kuroboshi, Manabu

AU - Utimoto, Kiitiro

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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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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

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