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Addition of Chloroprene Grignards to Aromatic Aldehydes: Synthesis of Homoallenyl Alcohols

Arne G. A. Geissler and Bernhard Breit*

*Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, Freiburg 79104, Germany, Email: bernhard.breitchemie.uni-freiburg.de

A. G. A. Geissler, B. Breit, Org. Lett., 2021, 23, 2621-2625.

DOI: 10.1021/acs.orglett.1c00527 (free Supporting Information)


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Abstract

Racemic homoallenyl alcohols can be synthesized from aldehydes and chloroprene-derived Grignards. The use of bis[2-dimethylaminoethyl]ether (BDMAEE) as an additive at low temperatures shifts the selectivity of the reaction almost exclusive toward allene formation. Simple and more elaborate methods for further derivatization enable quick access to more complex structures.

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proposed mechanism



Key Words

homoallylic alcohols, allenes


ID: J54-Y2021