Asymmetric acylation of carboxamides having trans-2,5-bis(methoxymethoxymethyl)pyrrolidine moiety as a chiral auxiliary and stereoselective reduction of the resulting 2-alkyl-3-oxoamides

Yoshio Ito; Tsutomu Katsuki; Masaru Yamaguchi

doi:10.1016/S0040-4039(01)81747-0

Asymmetric acylation of carboxamides having trans-2,5-bis(methoxymethoxymethyl)pyrrolidine moiety as a chiral auxiliary and stereoselective reduction of the resulting 2-alkyl-3-oxoamides

Yoshio Ito, Tsutomu Katsuki, Masaru Yamaguchi

Center for Environment and Safety

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60 Citations (Scopus)

Abstract

trans-2,5-Bis(methoxymethoxymethyl)pyrrolidine proved to be an excellent chiral auxiliary for the asymmetric acylation of the corresponding carboxamide enolates and the stereoselective Zn(BH₄)₂ reduction of the resulting 2-alkyl-3-oxo amides provided a useful alternative to asymmetric aldol reaction.

Original language	English
Pages (from-to)	6015-6016
Number of pages	2
Journal	Tetrahedron Letters
Volume	25
Issue number	52
DOIs	https://doi.org/10.1016/S0040-4039(01)81747-0
Publication status	Published - 1984

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All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

Ito, Y., Katsuki, T., & Yamaguchi, M. (1984). Asymmetric acylation of carboxamides having trans-2,5-bis(methoxymethoxymethyl)pyrrolidine moiety as a chiral auxiliary and stereoselective reduction of the resulting 2-alkyl-3-oxoamides. Tetrahedron Letters, 25(52), 6015-6016. https://doi.org/10.1016/S0040-4039(01)81747-0

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abstract = "trans-2,5-Bis(methoxymethoxymethyl)pyrrolidine proved to be an excellent chiral auxiliary for the asymmetric acylation of the corresponding carboxamide enolates and the stereoselective Zn(BH4)2 reduction of the resulting 2-alkyl-3-oxo amides provided a useful alternative to asymmetric aldol reaction.",

author = "Yoshio Ito and Tsutomu Katsuki and Masaru Yamaguchi",

year = "1984",

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AU - Ito, Yoshio

AU - Katsuki, Tsutomu

AU - Yamaguchi, Masaru

PY - 1984

Y1 - 1984

N2 - trans-2,5-Bis(methoxymethoxymethyl)pyrrolidine proved to be an excellent chiral auxiliary for the asymmetric acylation of the corresponding carboxamide enolates and the stereoselective Zn(BH4)2 reduction of the resulting 2-alkyl-3-oxo amides provided a useful alternative to asymmetric aldol reaction.

AB - trans-2,5-Bis(methoxymethoxymethyl)pyrrolidine proved to be an excellent chiral auxiliary for the asymmetric acylation of the corresponding carboxamide enolates and the stereoselective Zn(BH4)2 reduction of the resulting 2-alkyl-3-oxo amides provided a useful alternative to asymmetric aldol reaction.

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10.1016/S0040-4039(01)81747-0