Asymmetric alkylation of carboxyamides by using trans-2,5-disubstituted pyrrolidines as chiral auxiliaries

Yasuhiro Kawanami; Yoshio Ito; Toshiyuki Kitagawa; Yoshiyuki Taniguchi; Tsutomu Katsuki; Masaru Yamaguchi

doi:10.1016/S0040-4039(01)80046-0

Asymmetric alkylation of carboxyamides by using trans-2,5-disubstituted pyrrolidines as chiral auxiliaries

Yasuhiro Kawanami, Yoshio Ito, Toshiyuki Kitagawa, Yoshiyuki Taniguchi, Tsutomu Katsuki, Masaru Yamaguchi

Center of Environment and Safety

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

116 Citations (Scopus)

Abstract

trans-2,5-Bis(methoxymethyl)- and trans-2,5-bis(methoxymethoxymethyl)pyrrolidines proved to be excellent chiral auxiliaries for the asymmetric alkylation of the corresponding carboxyamide enolates giving good chemical yield and high stereoselectivity (invariably over 95% de), with remarkable flexibility to substrates and reaction conditions.

Original language	English
Pages (from-to)	857-860
Number of pages	4
Journal	Tetrahedron Letters
Volume	25
Issue number	8
DOIs	https://doi.org/10.1016/S0040-4039(01)80046-0
Publication status	Published - Jan 1 1984

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Asymmetric alkylation of carboxyamides by using trans-2,5-disubstituted pyrrolidines as chiral auxiliaries",

abstract = "trans-2,5-Bis(methoxymethyl)- and trans-2,5-bis(methoxymethoxymethyl)pyrrolidines proved to be excellent chiral auxiliaries for the asymmetric alkylation of the corresponding carboxyamide enolates giving good chemical yield and high stereoselectivity (invariably over 95% de), with remarkable flexibility to substrates and reaction conditions.",

author = "Yasuhiro Kawanami and Yoshio Ito and Toshiyuki Kitagawa and Yoshiyuki Taniguchi and Tsutomu Katsuki and Masaru Yamaguchi",

year = "1984",

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doi = "10.1016/S0040-4039(01)80046-0",

language = "English",

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pages = "857--860",

journal = "Tetrahedron Letters",

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T1 - Asymmetric alkylation of carboxyamides by using trans-2,5-disubstituted pyrrolidines as chiral auxiliaries

AU - Kawanami, Yasuhiro

AU - Ito, Yoshio

AU - Kitagawa, Toshiyuki

AU - Taniguchi, Yoshiyuki

AU - Katsuki, Tsutomu

AU - Yamaguchi, Masaru

PY - 1984/1/1

Y1 - 1984/1/1

N2 - trans-2,5-Bis(methoxymethyl)- and trans-2,5-bis(methoxymethoxymethyl)pyrrolidines proved to be excellent chiral auxiliaries for the asymmetric alkylation of the corresponding carboxyamide enolates giving good chemical yield and high stereoselectivity (invariably over 95% de), with remarkable flexibility to substrates and reaction conditions.

AB - trans-2,5-Bis(methoxymethyl)- and trans-2,5-bis(methoxymethoxymethyl)pyrrolidines proved to be excellent chiral auxiliaries for the asymmetric alkylation of the corresponding carboxyamide enolates giving good chemical yield and high stereoselectivity (invariably over 95% de), with remarkable flexibility to substrates and reaction conditions.

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U2 - 10.1016/S0040-4039(01)80046-0

DO - 10.1016/S0040-4039(01)80046-0

M3 - Article

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VL - 25

SP - 857

EP - 860

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 8

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