Rapid synthesis of macrocycles from diol precursors

Magnus Wingstrand; Charlotte Marie Madsen; Mads Hartvig Clausen

doi:10.1016/j.tetlet.2008.11.100

Rapid synthesis of macrocycles from diol precursors

Magnus Wingstrand, Charlotte Marie Madsen, Mads Hartvig Clausen

Department of Chemistry

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

A method for the formation of synthetic macrocycles with different ring sizes from diols is presented. Reacting a simple diol precursor with electrophilic reagents leads to a cyclic carbonate, sulfite or phosphate in a single step in 25-60% yield. Converting the cyclization precursor to a bis-electrophilic iodide or aldehyde enables preparation of a cyclic sulfide and amine, respectively, the latter using a double reductive amination to induce ring closure.

Original language	English
Journal	Tetrahedron Letters
Volume	50
Issue number	6
Pages (from-to)	693-695
ISSN	0040-4039
DOIs	https://doi.org/10.1016/j.tetlet.2008.11.100
Publication status	Published - 2009

Keywords

Macrocyclization
Reductive amination
Cyclic esters

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abstract = "A method for the formation of synthetic macrocycles with different ring sizes from diols is presented. Reacting a simple diol precursor with electrophilic reagents leads to a cyclic carbonate, sulfite or phosphate in a single step in 25-60% yield. Converting the cyclization precursor to a bis-electrophilic iodide or aldehyde enables preparation of a cyclic sulfide and amine, respectively, the latter using a double reductive amination to induce ring closure.",

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AU - Wingstrand, Magnus

AU - Madsen, Charlotte Marie

AU - Clausen, Mads Hartvig

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N2 - A method for the formation of synthetic macrocycles with different ring sizes from diols is presented. Reacting a simple diol precursor with electrophilic reagents leads to a cyclic carbonate, sulfite or phosphate in a single step in 25-60% yield. Converting the cyclization precursor to a bis-electrophilic iodide or aldehyde enables preparation of a cyclic sulfide and amine, respectively, the latter using a double reductive amination to induce ring closure.

AB - A method for the formation of synthetic macrocycles with different ring sizes from diols is presented. Reacting a simple diol precursor with electrophilic reagents leads to a cyclic carbonate, sulfite or phosphate in a single step in 25-60% yield. Converting the cyclization precursor to a bis-electrophilic iodide or aldehyde enables preparation of a cyclic sulfide and amine, respectively, the latter using a double reductive amination to induce ring closure.

KW - Macrocyclization

KW - Reductive amination

KW - Cyclic esters

U2 - 10.1016/j.tetlet.2008.11.100

DO - 10.1016/j.tetlet.2008.11.100

M3 - Journal article

SN - 0040-4039

VL - 50

SP - 693

EP - 695

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 6

ER -

Rapid synthesis of macrocycles from diol precursors

Abstract

Keywords

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