Asymmetric synthesis of multifunctionalized pyrrolines by a ruthenium porphyrin-catalyzed three-component coupling reaction

Hai Wei Xu; Gong Yong Li; Man Kin Wong; Chi Ming Che

doi:10.1021/ol050819n

Asymmetric synthesis of multifunctionalized pyrrolines by a ruthenium porphyrin-catalyzed three-component coupling reaction

Hai Wei Xu, Gong Yong Li, Man Kin Wong, Chi Ming Che

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

42 Citations (Scopus)

Abstract

(Chemical Equation Presented) Chiral multifunctionalized pyrrolines have been synthesized by a ruthenium porphyrin catalyzed three-component coupling reaction. In a one-pot reaction, ruthenium porphyrins catalyzed in situ generation of chiral azomethine ylides from chiral diazo esters and imines. Asymmetric 1,3-dipolar cycloaddition reactions of the chiral azomethine ylides with dipolarophiles afforded the corresponding pyrrolines in good yields and high diastereoselectivity (up to 92% de).

Original language	English
Pages (from-to)	5349-5352
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	24
DOIs	https://doi.org/10.1021/ol050819n
Publication status	Published - 24 Nov 2005
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol050819n

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abstract = "(Chemical Equation Presented) Chiral multifunctionalized pyrrolines have been synthesized by a ruthenium porphyrin catalyzed three-component coupling reaction. In a one-pot reaction, ruthenium porphyrins catalyzed in situ generation of chiral azomethine ylides from chiral diazo esters and imines. Asymmetric 1,3-dipolar cycloaddition reactions of the chiral azomethine ylides with dipolarophiles afforded the corresponding pyrrolines in good yields and high diastereoselectivity (up to 92% de).",

author = "Xu, {Hai Wei} and Li, {Gong Yong} and Wong, {Man Kin} and Che, {Chi Ming}",

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T1 - Asymmetric synthesis of multifunctionalized pyrrolines by a ruthenium porphyrin-catalyzed three-component coupling reaction

AU - Xu, Hai Wei

AU - Li, Gong Yong

AU - Wong, Man Kin

AU - Che, Chi Ming

PY - 2005/11/24

Y1 - 2005/11/24

N2 - (Chemical Equation Presented) Chiral multifunctionalized pyrrolines have been synthesized by a ruthenium porphyrin catalyzed three-component coupling reaction. In a one-pot reaction, ruthenium porphyrins catalyzed in situ generation of chiral azomethine ylides from chiral diazo esters and imines. Asymmetric 1,3-dipolar cycloaddition reactions of the chiral azomethine ylides with dipolarophiles afforded the corresponding pyrrolines in good yields and high diastereoselectivity (up to 92% de).

AB - (Chemical Equation Presented) Chiral multifunctionalized pyrrolines have been synthesized by a ruthenium porphyrin catalyzed three-component coupling reaction. In a one-pot reaction, ruthenium porphyrins catalyzed in situ generation of chiral azomethine ylides from chiral diazo esters and imines. Asymmetric 1,3-dipolar cycloaddition reactions of the chiral azomethine ylides with dipolarophiles afforded the corresponding pyrrolines in good yields and high diastereoselectivity (up to 92% de).

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U2 - 10.1021/ol050819n

DO - 10.1021/ol050819n

M3 - Journal article

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JO - Organic Letters

JF - Organic Letters

IS - 24

ER -

Asymmetric synthesis of multifunctionalized pyrrolines by a ruthenium porphyrin-catalyzed three-component coupling reaction

Abstract

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