Transition-metal-catalyzed group transfer reactions for selective C-H bond functionalization of artemisinin

Yungen Liu; Wenbo Xiao; Man Kin Wong; Chi Ming Che

doi:10.1021/ol071269r

Transition-metal-catalyzed group transfer reactions for selective C-H bond functionalization of artemisinin

Yungen Liu, Wenbo Xiao, Man Kin Wong, Chi Ming Che

Research output: Journal article publication › Journal article › Academic research › peer-review

32 Citations (Scopus)

Abstract

Three types of novel artemisinin derivatives have been synthesized through transition-metal-catalyzed intramolecular carbenoid and nitrenoid C-H bond insertion reactions. With rhodium complexes as catalysts, lactone 11 was synthesized via carbene insertion reaction at the C16 position in 90% yield; oxazolidinone 13 was synthesized via nitrene insertion reaction at the C10 position in 87% yield based on 77% conversion; and sulfamidate 14 was synthesized via nitrene insertion reaction at the C8 position in 87% yield.

Original language	English
Pages (from-to)	4107-4110
Number of pages	4
Journal	Organic Letters
Volume	9
Issue number	21
DOIs	https://doi.org/10.1021/ol071269r
Publication status	Published - 11 Oct 2007
Externally published	Yes

ASJC Scopus subject areas

Molecular Medicine

More information

10.1021/ol071269r

Cite this

@article{d4f34b2510f54631ae450698d37984ff,

title = "Transition-metal-catalyzed group transfer reactions for selective C-H bond functionalization of artemisinin",

abstract = "Three types of novel artemisinin derivatives have been synthesized through transition-metal-catalyzed intramolecular carbenoid and nitrenoid C-H bond insertion reactions. With rhodium complexes as catalysts, lactone 11 was synthesized via carbene insertion reaction at the C16 position in 90% yield; oxazolidinone 13 was synthesized via nitrene insertion reaction at the C10 position in 87% yield based on 77% conversion; and sulfamidate 14 was synthesized via nitrene insertion reaction at the C8 position in 87% yield.",

author = "Yungen Liu and Wenbo Xiao and Wong, {Man Kin} and Che, {Chi Ming}",

year = "2007",

month = oct,

day = "11",

doi = "10.1021/ol071269r",

language = "English",

volume = "9",

pages = "4107--4110",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "21",

}

TY - JOUR

T1 - Transition-metal-catalyzed group transfer reactions for selective C-H bond functionalization of artemisinin

AU - Liu, Yungen

AU - Xiao, Wenbo

AU - Wong, Man Kin

AU - Che, Chi Ming

PY - 2007/10/11

Y1 - 2007/10/11

N2 - Three types of novel artemisinin derivatives have been synthesized through transition-metal-catalyzed intramolecular carbenoid and nitrenoid C-H bond insertion reactions. With rhodium complexes as catalysts, lactone 11 was synthesized via carbene insertion reaction at the C16 position in 90% yield; oxazolidinone 13 was synthesized via nitrene insertion reaction at the C10 position in 87% yield based on 77% conversion; and sulfamidate 14 was synthesized via nitrene insertion reaction at the C8 position in 87% yield.

AB - Three types of novel artemisinin derivatives have been synthesized through transition-metal-catalyzed intramolecular carbenoid and nitrenoid C-H bond insertion reactions. With rhodium complexes as catalysts, lactone 11 was synthesized via carbene insertion reaction at the C16 position in 90% yield; oxazolidinone 13 was synthesized via nitrene insertion reaction at the C10 position in 87% yield based on 77% conversion; and sulfamidate 14 was synthesized via nitrene insertion reaction at the C8 position in 87% yield.

UR - http://www.scopus.com/inward/record.url?scp=35548976772&partnerID=8YFLogxK

U2 - 10.1021/ol071269r

DO - 10.1021/ol071269r

M3 - Journal article

C2 - 17880226

SN - 1523-7060

VL - 9

SP - 4107

EP - 4110

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Transition-metal-catalyzed group transfer reactions for selective C-H bond functionalization of artemisinin

Abstract

ASJC Scopus subject areas

More information

Other files and links

Fingerprint

Cite this