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. 2014 Aug 15;16(16):4220-3.
doi: 10.1021/ol501925f. Epub 2014 Jul 31.

Asymmetric synthesis of first generation molecular motors

Thomas M Neubauer  1 , Thomas van Leeuwen, Depeng Zhao, Anouk S Lubbe, Jos C M Kistemaker, Ben L Feringa
Affiliations

Asymmetric synthesis of first generation molecular motors

Thomas M Neubauer et al. Org Lett. .

Abstract

A general enantioselective route to functionalized first generation molecular motors is described. An enantioselective protonation of the silyl enol ethers of indanones by a Au(I)BINAP complex sets the stage for a highly diastereoselective McMurry coupling as a second enhancement step for enantiomeric excess. In this way various functionalized overcrowded alkenes could be synthesized in good yields (up to 78%) and good to excellent enantiomeric excess (85% ee->98% ee) values.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1. Rotary Cycle of Molecular Motor
Scheme 2
Scheme 2. Protective Group Manipulation of the Troc-indanones 9 and 10
Scheme 3
Scheme 3. McMurry Coupling Using LiAlH4 as Reductant
Scheme 4
Scheme 4. Proposed Mechanism of the Amplification
See this image and copyright information in PMC

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