A stereodivergent cascade imine → azomethine ylide → 1,3-dipolar cycloadditive approach to α-chiral pyrrolidines

Philip Garner; H. Ümit Kaniskan

doi:10.1016/j.tetlet.2005.05.119

A stereodivergent cascade imine → azomethine ylide → 1,3-dipolar cycloadditive approach to α-chiral pyrrolidines

Philip Garner
, H. Ümit Kaniskan

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

27 Scopus citations

Abstract

Stereodivergent [3+2] cycloadditions of chiral α-amino azomethine ylides leading to highly functionalized pyrrolidines are reported. The marriage of substrate conformational preferences and either an inter- or intramolecular cycloaddition manifold leads to either the l (syn) or u (anti) relationship between the pyrrolidine and α-stereocenters. The latter result may be applicable to a new approach to the bioxalomycin family of antibiotics.

Original language	English
Pages (from-to)	5181-5185
Number of pages	5
Journal	Tetrahedron Letters
Volume	46
Issue number	31
DOIs	https://doi.org/10.1016/j.tetlet.2005.05.119
State	Published - 1 Aug 2005
Externally published	Yes

Keywords

Chiral azomethine ylides
Pyrrolidine synthesis
Stereocontrolled [3+2] cycloadditions

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10.1016/j.tetlet.2005.05.119

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@article{dacc5f014ba141779eb3e8bf60253426,

title = "A stereodivergent cascade imine → azomethine ylide → 1,3-dipolar cycloadditive approach to α-chiral pyrrolidines",

abstract = "Stereodivergent [3+2] cycloadditions of chiral α-amino azomethine ylides leading to highly functionalized pyrrolidines are reported. The marriage of substrate conformational preferences and either an inter- or intramolecular cycloaddition manifold leads to either the l (syn) or u (anti) relationship between the pyrrolidine and α-stereocenters. The latter result may be applicable to a new approach to the bioxalomycin family of antibiotics.",

keywords = "Chiral azomethine ylides, Pyrrolidine synthesis, Stereocontrolled [3+2] cycloadditions",

author = "Philip Garner and Kaniskan, \{H. {\"U}mit\}",

note = "Funding Information: Acknowledgment is made to the donors of the American Chemical Society Petroleum Research Fund for support of this research. ",

year = "2005",

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day = "1",

doi = "10.1016/j.tetlet.2005.05.119",

language = "English",

volume = "46",

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journal = "Tetrahedron Letters",

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T1 - A stereodivergent cascade imine → azomethine ylide → 1,3-dipolar cycloadditive approach to α-chiral pyrrolidines

AU - Garner, Philip

AU - Kaniskan, H. Ümit

N1 - Funding Information: Acknowledgment is made to the donors of the American Chemical Society Petroleum Research Fund for support of this research.

PY - 2005/8/1

Y1 - 2005/8/1

N2 - Stereodivergent [3+2] cycloadditions of chiral α-amino azomethine ylides leading to highly functionalized pyrrolidines are reported. The marriage of substrate conformational preferences and either an inter- or intramolecular cycloaddition manifold leads to either the l (syn) or u (anti) relationship between the pyrrolidine and α-stereocenters. The latter result may be applicable to a new approach to the bioxalomycin family of antibiotics.

AB - Stereodivergent [3+2] cycloadditions of chiral α-amino azomethine ylides leading to highly functionalized pyrrolidines are reported. The marriage of substrate conformational preferences and either an inter- or intramolecular cycloaddition manifold leads to either the l (syn) or u (anti) relationship between the pyrrolidine and α-stereocenters. The latter result may be applicable to a new approach to the bioxalomycin family of antibiotics.

KW - Chiral azomethine ylides

KW - Pyrrolidine synthesis

KW - Stereocontrolled [3+2] cycloadditions

UR - https://www.scopus.com/pages/publications/21344472768

U2 - 10.1016/j.tetlet.2005.05.119

DO - 10.1016/j.tetlet.2005.05.119

M3 - Article

AN - SCOPUS:21344472768

SN - 0040-4039

VL - 46

SP - 5181

EP - 5185

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 31

ER -

A stereodivergent cascade imine → azomethine ylide → 1,3-dipolar cycloadditive approach to α-chiral pyrrolidines

Abstract

Keywords

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