Stereoselective synthesis of functionalized pyrrolidines by ruthenium porphyrin-catalyzed decomposition of α-diazo esters and cascade azomethine ylide formation/1,3-dipolar cycloaddition reactions

Gong Yong Li; Jian Chen; Wing Yiu Yu; Wei Hong; Chi Ming Che

doi:10.1021/ol034614v

Stereoselective synthesis of functionalized pyrrolidines by ruthenium porphyrin-catalyzed decomposition of α-diazo esters and cascade azomethine ylide formation/1,3-dipolar cycloaddition reactions

Gong Yong Li
, Jian Chen
, Wing Yiu Yu
, Wei Hong
, Chi Ming Che

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

72 Citations (Scopus)

Abstract

(Matrix presented) Ruthenium porphyrins catalyze three-component coupling reaction of α-diazo esters with a series of N-benzylidene imines and alkenes to form functionalized pyrrolidines in excellent diastereoselectivities. The reaction proceeds via a reactive ruthenium-carbene intermediate and its subsequent reaction with imine to generate azomethine ylide, which reacts with alkenes via 1,3-diploar cycloaddition.

Original language	English
Pages (from-to)	2153-2156
Number of pages	4
Journal	Organic Letters
Volume	5
Issue number	12
DOIs	https://doi.org/10.1021/ol034614v
Publication status	Published - 12 Jun 2003
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol034614v

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title = "Stereoselective synthesis of functionalized pyrrolidines by ruthenium porphyrin-catalyzed decomposition of α-diazo esters and cascade azomethine ylide formation/1,3-dipolar cycloaddition reactions",

abstract = "(Matrix presented) Ruthenium porphyrins catalyze three-component coupling reaction of α-diazo esters with a series of N-benzylidene imines and alkenes to form functionalized pyrrolidines in excellent diastereoselectivities. The reaction proceeds via a reactive ruthenium-carbene intermediate and its subsequent reaction with imine to generate azomethine ylide, which reacts with alkenes via 1,3-diploar cycloaddition.",

author = "Li, \{Gong Yong\} and Jian Chen and Yu, \{Wing Yiu\} and Wei Hong and Che, \{Chi Ming\}",

year = "2003",

month = jun,

day = "12",

doi = "10.1021/ol034614v",

language = "English",

volume = "5",

pages = "2153--2156",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "12",

}

Stereoselective synthesis of functionalized pyrrolidines by ruthenium porphyrin-catalyzed decomposition of α-diazo esters and cascade azomethine ylide formation/1,3-dipolar cycloaddition reactions. / Li, Gong Yong; Chen, Jian; Yu, Wing Yiu et al.
In: Organic Letters, Vol. 5, No. 12, 12.06.2003, p. 2153-2156.

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

TY - JOUR

T1 - Stereoselective synthesis of functionalized pyrrolidines by ruthenium porphyrin-catalyzed decomposition of α-diazo esters and cascade azomethine ylide formation/1,3-dipolar cycloaddition reactions

AU - Li, Gong Yong

AU - Chen, Jian

AU - Yu, Wing Yiu

AU - Hong, Wei

AU - Che, Chi Ming

PY - 2003/6/12

Y1 - 2003/6/12

N2 - (Matrix presented) Ruthenium porphyrins catalyze three-component coupling reaction of α-diazo esters with a series of N-benzylidene imines and alkenes to form functionalized pyrrolidines in excellent diastereoselectivities. The reaction proceeds via a reactive ruthenium-carbene intermediate and its subsequent reaction with imine to generate azomethine ylide, which reacts with alkenes via 1,3-diploar cycloaddition.

AB - (Matrix presented) Ruthenium porphyrins catalyze three-component coupling reaction of α-diazo esters with a series of N-benzylidene imines and alkenes to form functionalized pyrrolidines in excellent diastereoselectivities. The reaction proceeds via a reactive ruthenium-carbene intermediate and its subsequent reaction with imine to generate azomethine ylide, which reacts with alkenes via 1,3-diploar cycloaddition.

UR - https://www.scopus.com/pages/publications/0141519434

U2 - 10.1021/ol034614v

DO - 10.1021/ol034614v

M3 - Journal article

SN - 1523-7060

VL - 5

SP - 2153

EP - 2156

JO - Organic Letters

JF - Organic Letters

IS - 12

ER -

Stereoselective synthesis of functionalized pyrrolidines by ruthenium porphyrin-catalyzed decomposition of α-diazo esters and cascade azomethine ylide formation/1,3-dipolar cycloaddition reactions

Abstract

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