Synthesis of diastereomeric pheromones: adjacent methyl-branched alcohols and ketones

Submitting author affiliation:
Vietnam Academy of Science and Technology, Ho Chi Minh, Viet Nam

Beilstein Arch. 2019, 201964.

Published 09 Jul 2019

This preprint has not been peer-reviewed. When a peer-reviewed version is available, this information will be updated.


Racemic synthesis of adjacent methyl-branched alcohol and ketone pheromones is particularly considered for large scale trap of insects due to their similar activity to the chiral components in field trial. In this work, we presented a straightforward and effective strategy for racemic synthesis of adjacent methyl-branched alcohols to obtain the different diastereomer rates (threo: erythreo = 2:1 and 1:1) via Felkin-Anh model.  No effect of alkyl chain lenth on stereoselectivity of adduct has been demonstrated. Moreover, the α-methyl ketones were effectively produced by microwave-assisted oxidation of the respective secondary alcohols using 2-iodoxybenzoic acid (IBX)

Keywords: Grignard coupling, Felkin-Anh model, pheromone, microwave irradiation, stereoselectivity.

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When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

LE, V.-D.; Dang, C.-H.; Nguyen, C.-H.; Dang, V.-S.; Nguyen, T.-D. Beilstein Arch. 2019, 201964. doi:10.3762/bxiv.2019.64.v1

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