Synthesis of [4.6] spirocarbocycles: a base-promoted ring-expansion and subsequent I2-mediated regioselective spirocyclization protocol

Nana Fei; Zongkang Wang; Peng He; Qiongwen Kang; Yan Wang; Chengyu Wang; Yanzhong Li

doi:10.1039/d4qo01632g

Synthesis of [4.6] spirocarbocycles: a base-promoted ring-expansion and subsequent I₂-mediated regioselective spirocyclization protocol

Nana Fei
, Zongkang Wang
, Peng He
, Qiongwen Kang
, Yan Wang
, Chengyu Wang^*
, Yanzhong Li^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

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

3 Scopus citations

Abstract

An efficient protocol for the synthesis of [4.6] spirocarbocycles has been developed. This process is realized through the sequential K₂CO₃-promoted C-C σ-bond cleavage of cyclic ketoesters and an I₂-mediated selective 5-exo spirocyclization reaction at room temperature. Atom economy, C-C σ bond cleavage, regioselective spirocyclization, and mild and transition-metal-free reaction conditions are the advantages of this procedure.

Original language	English
Pages (from-to)	6797-6803
Number of pages	7
Journal	Organic Chemistry Frontiers
Volume	11
Issue number	23
DOIs	https://doi.org/10.1039/d4qo01632g
State	Published - 8 Oct 2024

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title = "Synthesis of [4.6] spirocarbocycles: a base-promoted ring-expansion and subsequent I2-mediated regioselective spirocyclization protocol",

abstract = "An efficient protocol for the synthesis of [4.6] spirocarbocycles has been developed. This process is realized through the sequential K2CO3-promoted C-C σ-bond cleavage of cyclic ketoesters and an I2-mediated selective 5-exo spirocyclization reaction at room temperature. Atom economy, C-C σ bond cleavage, regioselective spirocyclization, and mild and transition-metal-free reaction conditions are the advantages of this procedure.",

author = "Nana Fei and Zongkang Wang and Peng He and Qiongwen Kang and Yan Wang and Chengyu Wang and Yanzhong Li",

note = "Publisher Copyright: {\textcopyright} 2024 The Royal Society of Chemistry.",

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month = oct,

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doi = "10.1039/d4qo01632g",

language = "英语",

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T1 - Synthesis of [4.6] spirocarbocycles

T2 - a base-promoted ring-expansion and subsequent I2-mediated regioselective spirocyclization protocol

AU - Fei, Nana

AU - Wang, Zongkang

AU - He, Peng

AU - Kang, Qiongwen

AU - Wang, Yan

AU - Wang, Chengyu

AU - Li, Yanzhong

PY - 2024/10/8

Y1 - 2024/10/8

N2 - An efficient protocol for the synthesis of [4.6] spirocarbocycles has been developed. This process is realized through the sequential K2CO3-promoted C-C σ-bond cleavage of cyclic ketoesters and an I2-mediated selective 5-exo spirocyclization reaction at room temperature. Atom economy, C-C σ bond cleavage, regioselective spirocyclization, and mild and transition-metal-free reaction conditions are the advantages of this procedure.

AB - An efficient protocol for the synthesis of [4.6] spirocarbocycles has been developed. This process is realized through the sequential K2CO3-promoted C-C σ-bond cleavage of cyclic ketoesters and an I2-mediated selective 5-exo spirocyclization reaction at room temperature. Atom economy, C-C σ bond cleavage, regioselective spirocyclization, and mild and transition-metal-free reaction conditions are the advantages of this procedure.

UR - https://www.scopus.com/pages/publications/85206447464

U2 - 10.1039/d4qo01632g

DO - 10.1039/d4qo01632g

M3 - 文章

AN - SCOPUS:85206447464

SN - 2052-4110

VL - 11

SP - 6797

EP - 6803

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

IS - 23

ER -

Synthesis of [4.6] spirocarbocycles: a base-promoted ring-expansion and subsequent I₂-mediated regioselective spirocyclization protocol

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