Ruthenium(II) porphyrin catalyzed formation of (Z)-4-alkyloxycarbonyl-methylidene-1,3-dioxolanes from γ-alkoxy-γ-diazo-β-ketoesters

Shi Long Zheng; Wing Yiu Yu; Chi Ming Che

doi:10.1021/ol010283f

Ruthenium(II) porphyrin catalyzed formation of (Z)-4-alkyloxycarbonyl-methylidene-1,3-dioxolanes from γ-alkoxy-γ-diazo-β-ketoesters

Shi Long Zheng
, Wing Yiu Yu
, Chi Ming Che

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

33 Citations (Scopus)

Abstract

(equation presented) R1= aryl, allyl R2= methyl, 2,4-dimethyl-3-pentyl and (-)-menthyl Ruthenum(II) porphyrins and dirhodium(II) acetate catalyze cyclization of γ-alkoxy-α-diazo-β-ketoesters to (Z)-4-(alkyloxycarbonylmethylidene)-1,3-dioxolanes selectively (ca. 68% yield) with no formation of 3(2H)-furanones. Reacting a diazo ketoester with [RuII(TTP)(CO)] [H2TTP = meso-tetrakis(p-tolyl) porphyrin] in toluene afforded a ruthenium carbenoid complex, which has been isolated and spectroscopically characterized. A mechanism involving hydrogen atom migration from the C-H bond to the ruthenium carbenoid is proposed.

Original language	English
Pages (from-to)	889-892
Number of pages	4
Journal	Organic Letters
Volume	4
Issue number	6
DOIs	https://doi.org/10.1021/ol010283f
Publication status	Published - 21 Mar 2002
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol010283f

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@article{20f0160065d44ab0816d890175ccf609,

title = "Ruthenium(II) porphyrin catalyzed formation of (Z)-4-alkyloxycarbonyl-methylidene-1,3-dioxolanes from γ-alkoxy-γ-diazo-β-ketoesters",

abstract = "(equation presented) R1= aryl, allyl R2= methyl, 2,4-dimethyl-3-pentyl and (-)-menthyl Ruthenum(II) porphyrins and dirhodium(II) acetate catalyze cyclization of γ-alkoxy-α-diazo-β-ketoesters to (Z)-4-(alkyloxycarbonylmethylidene)-1,3-dioxolanes selectively (ca. 68\% yield) with no formation of 3(2H)-furanones. Reacting a diazo ketoester with [RuII(TTP)(CO)] [H2TTP = meso-tetrakis(p-tolyl) porphyrin] in toluene afforded a ruthenium carbenoid complex, which has been isolated and spectroscopically characterized. A mechanism involving hydrogen atom migration from the C-H bond to the ruthenium carbenoid is proposed.",

author = "Zheng, \{Shi Long\} and Yu, \{Wing Yiu\} and Che, \{Chi Ming\}",

year = "2002",

month = mar,

day = "21",

doi = "10.1021/ol010283f",

language = "English",

volume = "4",

pages = "889--892",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "6",

}

TY - JOUR

T1 - Ruthenium(II) porphyrin catalyzed formation of (Z)-4-alkyloxycarbonyl-methylidene-1,3-dioxolanes from γ-alkoxy-γ-diazo-β-ketoesters

AU - Zheng, Shi Long

AU - Yu, Wing Yiu

AU - Che, Chi Ming

PY - 2002/3/21

Y1 - 2002/3/21

N2 - (equation presented) R1= aryl, allyl R2= methyl, 2,4-dimethyl-3-pentyl and (-)-menthyl Ruthenum(II) porphyrins and dirhodium(II) acetate catalyze cyclization of γ-alkoxy-α-diazo-β-ketoesters to (Z)-4-(alkyloxycarbonylmethylidene)-1,3-dioxolanes selectively (ca. 68% yield) with no formation of 3(2H)-furanones. Reacting a diazo ketoester with [RuII(TTP)(CO)] [H2TTP = meso-tetrakis(p-tolyl) porphyrin] in toluene afforded a ruthenium carbenoid complex, which has been isolated and spectroscopically characterized. A mechanism involving hydrogen atom migration from the C-H bond to the ruthenium carbenoid is proposed.

AB - (equation presented) R1= aryl, allyl R2= methyl, 2,4-dimethyl-3-pentyl and (-)-menthyl Ruthenum(II) porphyrins and dirhodium(II) acetate catalyze cyclization of γ-alkoxy-α-diazo-β-ketoesters to (Z)-4-(alkyloxycarbonylmethylidene)-1,3-dioxolanes selectively (ca. 68% yield) with no formation of 3(2H)-furanones. Reacting a diazo ketoester with [RuII(TTP)(CO)] [H2TTP = meso-tetrakis(p-tolyl) porphyrin] in toluene afforded a ruthenium carbenoid complex, which has been isolated and spectroscopically characterized. A mechanism involving hydrogen atom migration from the C-H bond to the ruthenium carbenoid is proposed.

UR - https://www.scopus.com/pages/publications/0001080627

U2 - 10.1021/ol010283f

DO - 10.1021/ol010283f

M3 - Journal article

C2 - 11893178

SN - 1523-7060

VL - 4

SP - 889

EP - 892

JO - Organic Letters

JF - Organic Letters

IS - 6

ER -

Ruthenium(II) porphyrin catalyzed formation of (Z)-4-alkyloxycarbonyl-methylidene-1,3-dioxolanes from γ-alkoxy-γ-diazo-β-ketoesters

Abstract

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