Study of substrate dependence on the diastereoselectivity of the ruthenium(II) porphyrin catalyzed tandem formation and 1,3-dipolar cycloaddition reactions of carbonyl ylides

Cong Ying Zhou; Philip Wai Hong Chan; Wing Yiu Yu; Chi Ming Che

Study of substrate dependence on the diastereoselectivity of the ruthenium(II) porphyrin catalyzed tandem formation and 1,3-dipolar cycloaddition reactions of carbonyl ylides

Cong Ying Zhou, Philip Wai Hong Chan, Wing Yiu Yu, Chi Ming Che

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

Abstract

The effect of substrate substitution on reaction selectivity for the ruthenium(II) porphyrin catalyzed tandem carbonyl ylide formation/1,3-dipolar cycloaddition reaction of a variety of alkyl and aryl substituted α-diazo ketones 1 with π-unsaturated compounds was examined. The results suggested the diastereoselectivity of the reaction to be highly substrate dependant. Similar yields and cis/trans selectivities have also been achieved for the analogous reactions with rhodium(II,II) dimer as catalyst.

Original language	English
Pages (from-to)	1403-1412
Number of pages	10
Journal	Synthesis
Issue number	9
Publication status	Published - 22 Jul 2003
Externally published	Yes

Keywords

1,3-dipolar cycloaddition
Carbonyl ylide formation
Metallocarbenoids
Rhodium(II,II) dimers
Ruthenium(II) porphyrins

Cite this

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title = "Study of substrate dependence on the diastereoselectivity of the ruthenium(II) porphyrin catalyzed tandem formation and 1,3-dipolar cycloaddition reactions of carbonyl ylides",

abstract = "The effect of substrate substitution on reaction selectivity for the ruthenium(II) porphyrin catalyzed tandem carbonyl ylide formation/1,3-dipolar cycloaddition reaction of a variety of alkyl and aryl substituted α-diazo ketones 1 with π-unsaturated compounds was examined. The results suggested the diastereoselectivity of the reaction to be highly substrate dependant. Similar yields and cis/trans selectivities have also been achieved for the analogous reactions with rhodium(II,II) dimer as catalyst.",

keywords = "1,3-dipolar cycloaddition, Carbonyl ylide formation, Metallocarbenoids, Rhodium(II,II) dimers, Ruthenium(II) porphyrins",

author = "Zhou, {Cong Ying} and Chan, {Philip Wai Hong} and Yu, {Wing Yiu} and Che, {Chi Ming}",

year = "2003",

month = jul,

day = "22",

language = "English",

pages = "1403--1412",

journal = "Synthesis",

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publisher = "Georg Thieme",

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T1 - Study of substrate dependence on the diastereoselectivity of the ruthenium(II) porphyrin catalyzed tandem formation and 1,3-dipolar cycloaddition reactions of carbonyl ylides

AU - Zhou, Cong Ying

AU - Chan, Philip Wai Hong

AU - Yu, Wing Yiu

AU - Che, Chi Ming

PY - 2003/7/22

Y1 - 2003/7/22

N2 - The effect of substrate substitution on reaction selectivity for the ruthenium(II) porphyrin catalyzed tandem carbonyl ylide formation/1,3-dipolar cycloaddition reaction of a variety of alkyl and aryl substituted α-diazo ketones 1 with π-unsaturated compounds was examined. The results suggested the diastereoselectivity of the reaction to be highly substrate dependant. Similar yields and cis/trans selectivities have also been achieved for the analogous reactions with rhodium(II,II) dimer as catalyst.

AB - The effect of substrate substitution on reaction selectivity for the ruthenium(II) porphyrin catalyzed tandem carbonyl ylide formation/1,3-dipolar cycloaddition reaction of a variety of alkyl and aryl substituted α-diazo ketones 1 with π-unsaturated compounds was examined. The results suggested the diastereoselectivity of the reaction to be highly substrate dependant. Similar yields and cis/trans selectivities have also been achieved for the analogous reactions with rhodium(II,II) dimer as catalyst.

KW - 1,3-dipolar cycloaddition

KW - Carbonyl ylide formation

KW - Metallocarbenoids

KW - Rhodium(II,II) dimers

KW - Ruthenium(II) porphyrins

UR - http://www.scopus.com/inward/record.url?scp=0038575262&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0038575262

SN - 0039-7881

SP - 1403

EP - 1412

JO - Synthesis

JF - Synthesis

IS - 9

ER -

Study of substrate dependence on the diastereoselectivity of the ruthenium(II) porphyrin catalyzed tandem formation and 1,3-dipolar cycloaddition reactions of carbonyl ylides

Abstract

Keywords

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