Net directed 180° aryl-aryl bond rotation in a prototypical achiral biaryl lactone synthetic molecular motor

Ying Lin, Bart J. Dahl, Bruce Branchaud

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

Net directed 180° bond rotation was achieved through diastereoselective ring-opening reactions in an achiral biaryl lactone using a chiral nucleophile followed by re-lactonization. The efficiency of the directed bond rotation has been determined by HPLC-MS to be 50% and 20% with two different chiral nucleophiles. These results demonstrate the potential for a prototype of a chemically driven synthetic molecular motor which has the advantages of both simplicity and flexibility in operation and is the first example of the use of a chiral auxiliary to induce transient axial chirality resulting in net directed bond rotation.

Original languageEnglish (US)
Pages (from-to)8359-8362
Number of pages4
JournalTetrahedron Letters
Volume46
Issue number48
DOIs
StatePublished - Nov 28 2005
Externally publishedYes

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Lactones
Nucleophiles
Chirality
High Pressure Liquid Chromatography

Keywords

  • Directed bond rotation
  • Molecular machines
  • Molecular motors

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Net directed 180° aryl-aryl bond rotation in a prototypical achiral biaryl lactone synthetic molecular motor. / Lin, Ying; Dahl, Bart J.; Branchaud, Bruce.

In: Tetrahedron Letters, Vol. 46, No. 48, 28.11.2005, p. 8359-8362.

Research output: Contribution to journalArticle

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