Conjugate addition of organocopper reagents to n-tosylated α, β-unsaturated amides

Hideo Nagashima; Nobuyasu Ozaki; Masayoshi Washiyama; Kenji ltoh

doi:10.1016/S0040-4039(00)89172-8

Conjugate addition of organocopper reagents to n-tosylated α, β-unsaturated amides

Hideo Nagashima, Nobuyasu Ozaki, Masayoshi Washiyama, Kenji ltoh

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

69 Citations (Scopus)

Abstract

N-Tosylated α, β-unsaturated amides and lactams undergo facile conjugate addition with R²CuLi or RMgX/CuI (cat.). Stereoselective synthesis of trans-β,γ-dialkyl-γ-lactams can be achieved by this procedure. The resulting N-tosylamide moiety is further transformed to alcohol and several carbonyl compounds by way of reduction or nucleophillic displacement.

Original language	English
Pages (from-to)	657-660
Number of pages	4
Journal	Tetrahedron Letters
Volume	26
Issue number	5
DOIs	https://doi.org/10.1016/S0040-4039(00)89172-8
Publication status	Published - 1985
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)89172-8

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abstract = "N-Tosylated α, β-unsaturated amides and lactams undergo facile conjugate addition with R2CuLi or RMgX/CuI (cat.). Stereoselective synthesis of trans-β,γ-dialkyl-γ-lactams can be achieved by this procedure. The resulting N-tosylamide moiety is further transformed to alcohol and several carbonyl compounds by way of reduction or nucleophillic displacement.",

author = "Hideo Nagashima and Nobuyasu Ozaki and Masayoshi Washiyama and Kenji ltoh",

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AU - Nagashima, Hideo

AU - Ozaki, Nobuyasu

AU - Washiyama, Masayoshi

AU - ltoh, Kenji

PY - 1985

Y1 - 1985

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AB - N-Tosylated α, β-unsaturated amides and lactams undergo facile conjugate addition with R2CuLi or RMgX/CuI (cat.). Stereoselective synthesis of trans-β,γ-dialkyl-γ-lactams can be achieved by this procedure. The resulting N-tosylamide moiety is further transformed to alcohol and several carbonyl compounds by way of reduction or nucleophillic displacement.

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ER -

Conjugate addition of organocopper reagents to n-tosylated α, β-unsaturated amides

Abstract

All Science Journal Classification (ASJC) codes

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