N-Heterocyclic carbene-catalyzed radical ring-opening acylation of oxime esters with aldehydes

Zhihao Zhang; Xin Zou; Zhenjiang Li; Yu Gao; Yuanyuan Qu; Yusheng Quan; Yi Zhou; Jinlan Li; Jie Sun; Kai Guo

doi:10.1039/d1qo01015h

N-Heterocyclic carbene-catalyzed radical ring-opening acylation of oxime esters with aldehydes

Zhihao Zhang, Xin Zou, Zhenjiang Li, Yu Gao, Yuanyuan Qu, Yusheng Quan, Yi Zhou, Jinlan Li, Jie Sun, Kai Guo

COLLEGE OF BIOTECHNOLOGY AND PHARMACEUTICAL ENGINEERING

Nanjing Tech University

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

20 Scopus citations

Abstract

A cross-coupling of cycloketone oxime esters with aldehydes catalyzed by N-heterocyclic carbenes via a radical pathway was established. This modular protocol features easy operation, no external oxidants or reductants, and a broad functional group compatibility. The merit of this method was showcased by late-stage modification of complicated aldehydes derived from the medical intermediate pregnenolone and natural product diacetone-d-glucose.

Original language	English
Pages (from-to)	6074-6079
Number of pages	6
Journal	Organic Chemistry Frontiers
Volume	8
Issue number	21
DOIs	https://doi.org/10.1039/d1qo01015h
State	Published - 7 Nov 2021

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abstract = "A cross-coupling of cycloketone oxime esters with aldehydes catalyzed by N-heterocyclic carbenes via a radical pathway was established. This modular protocol features easy operation, no external oxidants or reductants, and a broad functional group compatibility. The merit of this method was showcased by late-stage modification of complicated aldehydes derived from the medical intermediate pregnenolone and natural product diacetone-d-glucose.",

author = "Zhihao Zhang and Xin Zou and Zhenjiang Li and Yu Gao and Yuanyuan Qu and Yusheng Quan and Yi Zhou and Jinlan Li and Jie Sun and Kai Guo",

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T1 - N-Heterocyclic carbene-catalyzed radical ring-opening acylation of oxime esters with aldehydes

AU - Zhang, Zhihao

AU - Zou, Xin

AU - Li, Zhenjiang

AU - Gao, Yu

AU - Qu, Yuanyuan

AU - Quan, Yusheng

AU - Zhou, Yi

AU - Li, Jinlan

AU - Sun, Jie

AU - Guo, Kai

PY - 2021/11/7

Y1 - 2021/11/7

N2 - A cross-coupling of cycloketone oxime esters with aldehydes catalyzed by N-heterocyclic carbenes via a radical pathway was established. This modular protocol features easy operation, no external oxidants or reductants, and a broad functional group compatibility. The merit of this method was showcased by late-stage modification of complicated aldehydes derived from the medical intermediate pregnenolone and natural product diacetone-d-glucose.

AB - A cross-coupling of cycloketone oxime esters with aldehydes catalyzed by N-heterocyclic carbenes via a radical pathway was established. This modular protocol features easy operation, no external oxidants or reductants, and a broad functional group compatibility. The merit of this method was showcased by late-stage modification of complicated aldehydes derived from the medical intermediate pregnenolone and natural product diacetone-d-glucose.

UR - http://www.scopus.com/inward/record.url?scp=85118292991&partnerID=8YFLogxK

U2 - 10.1039/d1qo01015h

DO - 10.1039/d1qo01015h

M3 - 文章

AN - SCOPUS:85118292991

SN - 2052-4110

VL - 8

SP - 6074

EP - 6079

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

IS - 21

ER -

N-Heterocyclic carbene-catalyzed radical ring-opening acylation of oxime esters with aldehydes

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