Unique stereocontrol in lanthanide(III)-catalyzed aldol reactions with the ketene silyl acetal of methyl (R)-3-hydroxybutanoate

Jin Hua Gu; Masahiro Terada; Koichi Mikami; Takeshi Nakai

doi:10.1016/S0040-4039(00)91648-4

Unique stereocontrol in lanthanide(III)-catalyzed aldol reactions with the ketene silyl acetal of methyl (R)-3-hydroxybutanoate

Jin Hua Gu, Masahiro Terada, Koichi Mikami, Takeshi Nakai

SCI - Chemistry

Tokyo Institute of Technology

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

28 Citations (Scopus)

Abstract

The Eu(III)-catalyzed reaction of α-benzyloxyaldehydes with the (R)-3-hydroxybutanoate-derived ketene silyl acetal is shown to provide a higher level of both "anti" diastereofacial selection and rather unusual anti diastereoselection, compared with the conventional TiCl₄-promoted version. The aldol adducts are elaborated to the carbapenem intermediates.

Original language	English
Pages (from-to)	1465-1468
Number of pages	4
Journal	Tetrahedron Letters
Volume	33
Issue number	11
DOIs	https://doi.org/10.1016/S0040-4039(00)91648-4
Publication status	Published - 1992 Mar 10

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abstract = "The Eu(III)-catalyzed reaction of α-benzyloxyaldehydes with the (R)-3-hydroxybutanoate-derived ketene silyl acetal is shown to provide a higher level of both {"}anti{"} diastereofacial selection and rather unusual anti diastereoselection, compared with the conventional TiCl4-promoted version. The aldol adducts are elaborated to the carbapenem intermediates.",

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AU - Terada, Masahiro

AU - Mikami, Koichi

AU - Nakai, Takeshi

PY - 1992/3/10

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N2 - The Eu(III)-catalyzed reaction of α-benzyloxyaldehydes with the (R)-3-hydroxybutanoate-derived ketene silyl acetal is shown to provide a higher level of both "anti" diastereofacial selection and rather unusual anti diastereoselection, compared with the conventional TiCl4-promoted version. The aldol adducts are elaborated to the carbapenem intermediates.

AB - The Eu(III)-catalyzed reaction of α-benzyloxyaldehydes with the (R)-3-hydroxybutanoate-derived ketene silyl acetal is shown to provide a higher level of both "anti" diastereofacial selection and rather unusual anti diastereoselection, compared with the conventional TiCl4-promoted version. The aldol adducts are elaborated to the carbapenem intermediates.

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Unique stereocontrol in lanthanide(III)-catalyzed aldol reactions with the ketene silyl acetal of methyl (R)-3-hydroxybutanoate

Abstract

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