Ruthenium porphyrin catalyzed intramolecular carbenoid C-H insertion. Stereoselective synthesis of Cis-disubstituted oxygen and nitrogen heterocycles

Wai Hung Cheung; Shi Long Zheng; Wing Yiu Yu; Guo Chuan Zhou; Chi Ming Che

doi:10.1021/ol034806q

Ruthenium porphyrin catalyzed intramolecular carbenoid C-H insertion. Stereoselective synthesis of Cis-disubstituted oxygen and nitrogen heterocycles

Wai Hung Cheung
, Shi Long Zheng
, Wing Yiu Yu
, Guo Chuan Zhou
, Chi Ming Che

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

125 Citations (Scopus)

Abstract

(Matrix presented) A ruthenium porphyrin-catalyzed stereoselective intramolecular carbenoid C-H insertion is described. Using [RuII(TTP)(CO)] as catalyst, aryl tosylhydrazones are converted to 2,3-dihydrobenzofurans, 2,3-dihydroindoles, and β-lactams in good yields and remarkable cis selectivity (up to 99%). Enantioselective synthesis of 2,3-dihydrobenzofurans is also achieved with [RuII(D4-Por*)(CO)] as catalyst, and up to 96% ee is attained.

Original language	English
Pages (from-to)	2535-2538
Number of pages	4
Journal	Organic Letters
Volume	5
Issue number	14
DOIs	https://doi.org/10.1021/ol034806q
Publication status	Published - 10 Jul 2003
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol034806q

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title = "Ruthenium porphyrin catalyzed intramolecular carbenoid C-H insertion. Stereoselective synthesis of Cis-disubstituted oxygen and nitrogen heterocycles",

abstract = "(Matrix presented) A ruthenium porphyrin-catalyzed stereoselective intramolecular carbenoid C-H insertion is described. Using [RuII(TTP)(CO)] as catalyst, aryl tosylhydrazones are converted to 2,3-dihydrobenzofurans, 2,3-dihydroindoles, and β-lactams in good yields and remarkable cis selectivity (up to 99\%). Enantioselective synthesis of 2,3-dihydrobenzofurans is also achieved with [RuII(D4-Por*)(CO)] as catalyst, and up to 96\% ee is attained.",

author = "Cheung, \{Wai Hung\} and Zheng, \{Shi Long\} and Yu, \{Wing Yiu\} and Zhou, \{Guo Chuan\} and Che, \{Chi Ming\}",

year = "2003",

month = jul,

day = "10",

doi = "10.1021/ol034806q",

language = "English",

volume = "5",

pages = "2535--2538",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "14",

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Ruthenium porphyrin catalyzed intramolecular carbenoid C-H insertion. Stereoselective synthesis of Cis-disubstituted oxygen and nitrogen heterocycles. / Cheung, Wai Hung; Zheng, Shi Long; Yu, Wing Yiu et al.
In: Organic Letters, Vol. 5, No. 14, 10.07.2003, p. 2535-2538.

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

TY - JOUR

T1 - Ruthenium porphyrin catalyzed intramolecular carbenoid C-H insertion. Stereoselective synthesis of Cis-disubstituted oxygen and nitrogen heterocycles

AU - Cheung, Wai Hung

AU - Zheng, Shi Long

AU - Yu, Wing Yiu

AU - Zhou, Guo Chuan

AU - Che, Chi Ming

PY - 2003/7/10

Y1 - 2003/7/10

N2 - (Matrix presented) A ruthenium porphyrin-catalyzed stereoselective intramolecular carbenoid C-H insertion is described. Using [RuII(TTP)(CO)] as catalyst, aryl tosylhydrazones are converted to 2,3-dihydrobenzofurans, 2,3-dihydroindoles, and β-lactams in good yields and remarkable cis selectivity (up to 99%). Enantioselective synthesis of 2,3-dihydrobenzofurans is also achieved with [RuII(D4-Por*)(CO)] as catalyst, and up to 96% ee is attained.

AB - (Matrix presented) A ruthenium porphyrin-catalyzed stereoselective intramolecular carbenoid C-H insertion is described. Using [RuII(TTP)(CO)] as catalyst, aryl tosylhydrazones are converted to 2,3-dihydrobenzofurans, 2,3-dihydroindoles, and β-lactams in good yields and remarkable cis selectivity (up to 99%). Enantioselective synthesis of 2,3-dihydrobenzofurans is also achieved with [RuII(D4-Por*)(CO)] as catalyst, and up to 96% ee is attained.

UR - https://www.scopus.com/pages/publications/0141742604

U2 - 10.1021/ol034806q

DO - 10.1021/ol034806q

M3 - Journal article

SN - 1523-7060

VL - 5

SP - 2535

EP - 2538

JO - Organic Letters

JF - Organic Letters

IS - 14

ER -

Ruthenium porphyrin catalyzed intramolecular carbenoid C-H insertion. Stereoselective synthesis of Cis-disubstituted oxygen and nitrogen heterocycles

Abstract

ASJC Scopus subject areas

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