Rapid synthesis of macrocycles from diol precursors

Magnus Wingstrand, Charlotte Marie Madsen, Mads Hartvig Clausen

Research output: Contribution to journalJournal articleResearchpeer-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 languageEnglish
JournalTetrahedron Letters
Volume50
Issue number6
Pages (from-to)693-695
ISSN0040-4039
DOIs
Publication statusPublished - 2009

Keywords

  • Macrocyclization
  • Reductive amination
  • Cyclic esters

Cite this

Wingstrand, Magnus ; Madsen, Charlotte Marie ; Clausen, Mads Hartvig. / Rapid synthesis of macrocycles from diol precursors. In: Tetrahedron Letters. 2009 ; Vol. 50, No. 6. pp. 693-695.
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Rapid synthesis of macrocycles from diol precursors. / Wingstrand, Magnus; Madsen, Charlotte Marie; Clausen, Mads Hartvig.

In: Tetrahedron Letters, Vol. 50, No. 6, 2009, p. 693-695.

Research output: Contribution to journalJournal articleResearchpeer-review

TY - JOUR

T1 - Rapid synthesis of macrocycles from diol precursors

AU - Wingstrand, Magnus

AU - Madsen, Charlotte Marie

AU - Clausen, Mads Hartvig

PY - 2009

Y1 - 2009

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

VL - 50

SP - 693

EP - 695

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 6

ER -