KOtBu-catalysed α-homoallylic alkylation of acyclic amides with 1-aryl-1,3-dienes

Yunfei Xiang; Ruisheng Du; Shang Wang; Xiang Wu; Jie Tang; Fan Yang; Dong Xing

doi:10.1007/s11030-022-10503-8

KOtBu-catalysed α-homoallylic alkylation of acyclic amides with 1-aryl-1,3-dienes

Yunfei Xiang
, Ruisheng Du
, Shang Wang
, Xiang Wu
, Jie Tang
, Fan Yang^*
, Dong Xing^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

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

1 Scopus citations

Abstract

Herein, we report a KOtBu-catalysed α-homoallylic alkylation of acyclic amides with 1-aryl-1,3-dienes. With this transition metal-free and atom-economic protocol, a series of α-homoallylic alkylated acyclic amides were synthesized in good to excellent yields. This transformation is proposed to proceed through a cation-π interaction-based C–C bond formation from the in situ-generated potassium enolate with the diene unit. Graphical abstract: [Figure not available: see fulltext.]

Original language	English
Pages (from-to)	1481-1487
Number of pages	7
Journal	Molecular Diversity
Volume	27
Issue number	3
DOIs	https://doi.org/10.1007/s11030-022-10503-8
State	Published - Jun 2023

Keywords

Amide
Diene
Homoallylic alkylation
KOtBu
Transition metal-free

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10.1007/s11030-022-10503-8

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title = "KOtBu-catalysed α-homoallylic alkylation of acyclic amides with 1-aryl-1,3-dienes",

abstract = "Herein, we report a KOtBu-catalysed α-homoallylic alkylation of acyclic amides with 1-aryl-1,3-dienes. With this transition metal-free and atom-economic protocol, a series of α-homoallylic alkylated acyclic amides were synthesized in good to excellent yields. This transformation is proposed to proceed through a cation-π interaction-based C–C bond formation from the in situ-generated potassium enolate with the diene unit. Graphical abstract: [Figure not available: see fulltext.]",

keywords = "Amide, Diene, Homoallylic alkylation, KOtBu, Transition metal-free",

author = "Yunfei Xiang and Ruisheng Du and Shang Wang and Xiang Wu and Jie Tang and Fan Yang and Dong Xing",

note = "Publisher Copyright: {\textcopyright} 2022, The Author(s), under exclusive licence to Springer Nature Switzerland AG.",

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doi = "10.1007/s11030-022-10503-8",

language = "英语",

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TY - JOUR

T1 - KOtBu-catalysed α-homoallylic alkylation of acyclic amides with 1-aryl-1,3-dienes

AU - Xiang, Yunfei

AU - Du, Ruisheng

AU - Wang, Shang

AU - Wu, Xiang

AU - Tang, Jie

AU - Yang, Fan

AU - Xing, Dong

PY - 2023/6

Y1 - 2023/6

N2 - Herein, we report a KOtBu-catalysed α-homoallylic alkylation of acyclic amides with 1-aryl-1,3-dienes. With this transition metal-free and atom-economic protocol, a series of α-homoallylic alkylated acyclic amides were synthesized in good to excellent yields. This transformation is proposed to proceed through a cation-π interaction-based C–C bond formation from the in situ-generated potassium enolate with the diene unit. Graphical abstract: [Figure not available: see fulltext.]

AB - Herein, we report a KOtBu-catalysed α-homoallylic alkylation of acyclic amides with 1-aryl-1,3-dienes. With this transition metal-free and atom-economic protocol, a series of α-homoallylic alkylated acyclic amides were synthesized in good to excellent yields. This transformation is proposed to proceed through a cation-π interaction-based C–C bond formation from the in situ-generated potassium enolate with the diene unit. Graphical abstract: [Figure not available: see fulltext.]

KW - Amide

KW - Diene

KW - Homoallylic alkylation

KW - KOtBu

KW - Transition metal-free

UR - https://www.scopus.com/pages/publications/85136982623

U2 - 10.1007/s11030-022-10503-8

DO - 10.1007/s11030-022-10503-8

M3 - 文章

C2 - 36001226

AN - SCOPUS:85136982623

SN - 1381-1991

VL - 27

SP - 1481

EP - 1487

JO - Molecular Diversity

JF - Molecular Diversity

IS - 3

ER -

KOtBu-catalysed α-homoallylic alkylation of acyclic amides with 1-aryl-1,3-dienes

Abstract

Keywords

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