Asymmetric Synthesis of First Generation Molecular Motors | Zendy

Thomas Neubauer | Zendy; Thomas Van Leeuwen | Zendy; Depeng Zhao | Zendy; Anouk S. Lubbe | Zendy; Jos C. M. Kistemaker | Zendy; Ben L. Feringa | Zendy

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Asymmetric Synthesis of First Generation Molecular Motors

Author(s) -

Thomas Neubauer,

Thomas Van Leeuwen,

Depeng Zhao,

Anouk S. Lubbe,

Jos C. M. Kistemaker,

Ben L. Feringa

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol501925f

Subject(s) - enantioselective synthesis , chemistry , protonation , enantiomer , enol , enantiomeric excess , silylation , combinatorial chemistry , organic chemistry , catalysis , ion

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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