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

Ying Lin; Bart J. Dahl; Bruce P. Branchaud

doi:10.1016/j.tetlet.2005.09.151

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

Ying Lin, Bart J. Dahl, Bruce P. Branchaud

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

27 Scopus citations

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 language	English (US)
Pages (from-to)	8359-8362
Number of pages	4
Journal	Tetrahedron Letters
Volume	46
Issue number	48
DOIs	https://doi.org/10.1016/j.tetlet.2005.09.151
State	Published - Nov 28 2005
Externally published	Yes

Keywords

Directed bond rotation
Molecular machines
Molecular motors

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2005.09.151

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

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.",

keywords = "Directed bond rotation, Molecular machines, Molecular motors",

author = "Ying Lin and Dahl, {Bart J.} and Branchaud, {Bruce P.}",

note = "Funding Information: We are grateful to NSF-CHE-9986926, PRF #35372AC-1, the US Department of Education GAANN P200A010222-03, and the NSF-IGERT DGE-0114419, for financial support. ",

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doi = "10.1016/j.tetlet.2005.09.151",

language = "English (US)",

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T1 - Net directed 180° aryl-aryl bond rotation in a prototypical achiral biaryl lactone synthetic molecular motor

AU - Lin, Ying

AU - Dahl, Bart J.

AU - Branchaud, Bruce P.

N1 - Funding Information: We are grateful to NSF-CHE-9986926, PRF #35372AC-1, the US Department of Education GAANN P200A010222-03, and the NSF-IGERT DGE-0114419, for financial support.

PY - 2005/11/28

Y1 - 2005/11/28

N2 - 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.

AB - 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.

KW - Directed bond rotation

KW - Molecular machines

KW - Molecular motors

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DO - 10.1016/j.tetlet.2005.09.151

M3 - Article

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SN - 0040-4039

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 48

ER -

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

Abstract

Keywords

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