Ruthenium(II) porphyrin catalyzed tandem carbonyl ylide formation and 1,3-dipolar cycloaddition reactions of α-diazo ketones

Cong Ying Zhou; Wing Yiu Yu; Chi Ming Che

doi:10.1021/ol0201254

Ruthenium(II) porphyrin catalyzed tandem carbonyl ylide formation and 1,3-dipolar cycloaddition reactions of α-diazo ketones

Cong Ying Zhou
, Wing Yiu Yu
, Chi Ming Che

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

52 Citations (Scopus)

Abstract

equation presented The ruthenium porphyrin-catalyzed reactions of diazo ketones with π-unsaturated compounds via carbonyl ylide formation/cycloaddition cascade exhibit product yields and selectivities comparable to the analogous reactions with dirhodium carboxylates as catalysts. By grafting a ruthenium porphyrin on poly(ethylene glycol) (Zhang, J.-L; Che, C.-M. Org. Lett. 2002, 4, 1911), a recyclable catalytic system is developed with over 5700 product turnovers attained for the reaction of 1-diazo-2,5-hexanedione with dimethyl acetylenedicarboxylate.

Original language	English
Pages (from-to)	3235-3238
Number of pages	4
Journal	Organic Letters
Volume	4
Issue number	19
DOIs	https://doi.org/10.1021/ol0201254
Publication status	Published - 19 Sept 2002
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol0201254

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title = "Ruthenium(II) porphyrin catalyzed tandem carbonyl ylide formation and 1,3-dipolar cycloaddition reactions of α-diazo ketones",

abstract = "equation presented The ruthenium porphyrin-catalyzed reactions of diazo ketones with π-unsaturated compounds via carbonyl ylide formation/cycloaddition cascade exhibit product yields and selectivities comparable to the analogous reactions with dirhodium carboxylates as catalysts. By grafting a ruthenium porphyrin on poly(ethylene glycol) (Zhang, J.-L; Che, C.-M. Org. Lett. 2002, 4, 1911), a recyclable catalytic system is developed with over 5700 product turnovers attained for the reaction of 1-diazo-2,5-hexanedione with dimethyl acetylenedicarboxylate.",

author = "Zhou, \{Cong Ying\} and Yu, \{Wing Yiu\} and Che, \{Chi Ming\}",

year = "2002",

month = sep,

day = "19",

doi = "10.1021/ol0201254",

language = "English",

volume = "4",

pages = "3235--3238",

journal = "Organic Letters",

issn = "1523-7060",

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T1 - Ruthenium(II) porphyrin catalyzed tandem carbonyl ylide formation and 1,3-dipolar cycloaddition reactions of α-diazo ketones

AU - Zhou, Cong Ying

AU - Yu, Wing Yiu

AU - Che, Chi Ming

PY - 2002/9/19

Y1 - 2002/9/19

N2 - equation presented The ruthenium porphyrin-catalyzed reactions of diazo ketones with π-unsaturated compounds via carbonyl ylide formation/cycloaddition cascade exhibit product yields and selectivities comparable to the analogous reactions with dirhodium carboxylates as catalysts. By grafting a ruthenium porphyrin on poly(ethylene glycol) (Zhang, J.-L; Che, C.-M. Org. Lett. 2002, 4, 1911), a recyclable catalytic system is developed with over 5700 product turnovers attained for the reaction of 1-diazo-2,5-hexanedione with dimethyl acetylenedicarboxylate.

AB - equation presented The ruthenium porphyrin-catalyzed reactions of diazo ketones with π-unsaturated compounds via carbonyl ylide formation/cycloaddition cascade exhibit product yields and selectivities comparable to the analogous reactions with dirhodium carboxylates as catalysts. By grafting a ruthenium porphyrin on poly(ethylene glycol) (Zhang, J.-L; Che, C.-M. Org. Lett. 2002, 4, 1911), a recyclable catalytic system is developed with over 5700 product turnovers attained for the reaction of 1-diazo-2,5-hexanedione with dimethyl acetylenedicarboxylate.

UR - https://www.scopus.com/pages/publications/0038221606

U2 - 10.1021/ol0201254

DO - 10.1021/ol0201254

M3 - Journal article

C2 - 12227757

SN - 1523-7060

VL - 4

SP - 3235

EP - 3238

JO - Organic Letters

JF - Organic Letters

IS - 19

ER -

Ruthenium(II) porphyrin catalyzed tandem carbonyl ylide formation and 1,3-dipolar cycloaddition reactions of α-diazo ketones

Abstract

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