Aldol reaction of iododifluoroacetate-Zn and 2,2-difluoroketene silyl acetal

Osamu Kitagawa; Takeo Taguchi; Yoshiro Kobayashi

doi:10.1016/S0040-4039(00)82048-1

Aldol reaction of iododifluoroacetate-Zn and 2,2-difluoroketene silyl acetal

Osamu Kitagawa, Takeo Taguchi, Yoshiro Kobayashi

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

115 Citations (Scopus)

Abstract

Generation of the Reformatsky reagent of difluoracetate from the iodide (2) and the difluoroketene silyl acetal (3), and their aldol reaction are described. High anti-selectivity with chiral aldehyde (5d, 5f) was found in the case of the ketene silyl acetal (3b). 2,2-Difluoro-2-deoxy analogs of D-ribo- and L-galactopyranosides (1a, 1b) were effectively prepared.

Original language	English
Pages (from-to)	1803-1806
Number of pages	4
Journal	Tetrahedron Letters
Volume	29
Issue number	15
DOIs	https://doi.org/10.1016/S0040-4039(00)82048-1
Publication status	Published - 1988
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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abstract = "Generation of the Reformatsky reagent of difluoracetate from the iodide (2) and the difluoroketene silyl acetal (3), and their aldol reaction are described. High anti-selectivity with chiral aldehyde (5d, 5f) was found in the case of the ketene silyl acetal (3b). 2,2-Difluoro-2-deoxy analogs of D-ribo- and L-galactopyranosides (1a, 1b) were effectively prepared.",

author = "Osamu Kitagawa and Takeo Taguchi and Yoshiro Kobayashi",

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doi = "10.1016/S0040-4039(00)82048-1",

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T1 - Aldol reaction of iododifluoroacetate-Zn and 2,2-difluoroketene silyl acetal

AU - Kitagawa, Osamu

AU - Taguchi, Takeo

AU - Kobayashi, Yoshiro

PY - 1988

Y1 - 1988

N2 - Generation of the Reformatsky reagent of difluoracetate from the iodide (2) and the difluoroketene silyl acetal (3), and their aldol reaction are described. High anti-selectivity with chiral aldehyde (5d, 5f) was found in the case of the ketene silyl acetal (3b). 2,2-Difluoro-2-deoxy analogs of D-ribo- and L-galactopyranosides (1a, 1b) were effectively prepared.

AB - Generation of the Reformatsky reagent of difluoracetate from the iodide (2) and the difluoroketene silyl acetal (3), and their aldol reaction are described. High anti-selectivity with chiral aldehyde (5d, 5f) was found in the case of the ketene silyl acetal (3b). 2,2-Difluoro-2-deoxy analogs of D-ribo- and L-galactopyranosides (1a, 1b) were effectively prepared.

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EP - 1806

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 15

ER -

Aldol reaction of iododifluoroacetate-Zn and 2,2-difluoroketene silyl acetal

Abstract

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