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 for Environment and Safety

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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

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All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

Kawanami, Y., Ito, Y., Kitagawa, T., Taniguchi, Y., Katsuki, T., & Yamaguchi, M. (1984). Asymmetric alkylation of carboxyamides by using trans-2,5-disubstituted pyrrolidines as chiral auxiliaries. Tetrahedron Letters, 25(8), 857-860. https://doi.org/10.1016/S0040-4039(01)80046-0

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AU - Kitagawa, Toshiyuki

AU - Taniguchi, Yoshiyuki

AU - Katsuki, Tsutomu

AU - Yamaguchi, Masaru

PY - 1984/1/1

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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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10.1016/S0040-4039(01)80046-0