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^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

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

4 Scopus citations

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.

Original language	English
Pages (from-to)	1642-1648
Number of pages	7
Journal	Organic Chemistry Frontiers
Volume	9
Issue number	6
DOIs	https://doi.org/10.1039/d1qo01927a
State	Published - 2 Feb 2022

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

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.",

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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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