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

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

64 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
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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title = "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",

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",

doi = "10.1016/S0040-4039(01)81747-0",

language = "English",

volume = "25",

pages = "6015--6016",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "52",

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TY - JOUR

T1 - 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

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.

UR - https://www.scopus.com/pages/publications/0000624803

UR - https://www.scopus.com/pages/publications/0000624803#tab=citedBy

U2 - 10.1016/S0040-4039(01)81747-0

DO - 10.1016/S0040-4039(01)81747-0

M3 - Article

AN - SCOPUS:0000624803

SN - 0040-4039

VL - 25

SP - 6015

EP - 6016

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 52

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

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