Construction of quaternary carbon centers by KOtBu-catalyzed α-homoallylic alkylation of lactams with 1,3-dienes

Shang Wang; Yunfei Xiang; Tiantian Chen; Xiang Wu; Dong Xing

doi:10.1039/d1qo01927a

Construction of quaternary carbon centers by KOtBu-catalyzed α-homoallylic alkylation of lactams with 1,3-dienes

Shang Wang
, Yunfei Xiang
, Tiantian Chen
, Xiang Wu
, Dong Xing^*

^*此作品的通讯作者

化学与分子工程学院

East China Normal University

科研成果: 期刊稿件 › 文章 › 同行评审

4 引用（Scopus）

摘要

We report a KOtBu-catalyzed α-homoallylic alkylation of lactams with 1,3-dienes. With this transition metal-free and atom-economical protocol, a variety of α-homoallylic alkylated lactams bearing α-quaternary carbon centers were formed in a 2,1-addition manner with excellent regioselectivity. A cation-π interaction between the in situ-generated potassium enolate and the diene is proposed to play a key role in accelerating this transformation.

源语言	英语
页（从-至）	1642-1648
页数	7
期刊	Organic Chemistry Frontiers
卷	9
期	6
DOI	https://doi.org/10.1039/d1qo01927a
出版状态	已出版 - 2 2月 2022

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abstract = "We report a KOtBu-catalyzed α-homoallylic alkylation of lactams with 1,3-dienes. With this transition metal-free and atom-economical protocol, a variety of α-homoallylic alkylated lactams bearing α-quaternary carbon centers were formed in a 2,1-addition manner with excellent regioselectivity. A cation-π interaction between the in situ-generated potassium enolate and the diene is proposed to play a key role in accelerating this transformation.",

author = "Shang Wang and Yunfei Xiang and Tiantian Chen and Xiang Wu and Dong Xing",

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T1 - Construction of quaternary carbon centers by KOtBu-catalyzed α-homoallylic alkylation of lactams with 1,3-dienes

AU - Wang, Shang

AU - Xiang, Yunfei

AU - Chen, Tiantian

AU - Wu, Xiang

AU - Xing, Dong

PY - 2022/2/2

Y1 - 2022/2/2

N2 - We report a KOtBu-catalyzed α-homoallylic alkylation of lactams with 1,3-dienes. With this transition metal-free and atom-economical protocol, a variety of α-homoallylic alkylated lactams bearing α-quaternary carbon centers were formed in a 2,1-addition manner with excellent regioselectivity. A cation-π interaction between the in situ-generated potassium enolate and the diene is proposed to play a key role in accelerating this transformation.

AB - We report a KOtBu-catalyzed α-homoallylic alkylation of lactams with 1,3-dienes. With this transition metal-free and atom-economical protocol, a variety of α-homoallylic alkylated lactams bearing α-quaternary carbon centers were formed in a 2,1-addition manner with excellent regioselectivity. A cation-π interaction between the in situ-generated potassium enolate and the diene is proposed to play a key role in accelerating this transformation.

UR - https://www.scopus.com/pages/publications/85127868115

U2 - 10.1039/d1qo01927a

DO - 10.1039/d1qo01927a

M3 - 文章

AN - SCOPUS:85127868115

SN - 2052-4110

VL - 9

SP - 1642

EP - 1648

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

IS - 6

ER -

Construction of quaternary carbon centers by KOtBu-catalyzed α-homoallylic alkylation of lactams with 1,3-dienes

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