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

  1. VAN-DUNG LEORCID Logo,
  2. Chi-Hien Dang,
  3. Cong-Hao Nguyen,
  4. Van-Su Dang and
  5. Thanh-Danh Nguyen ORCID Logo

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

Beilstein Arch. 2019, 201964. doi:10.3762/bxiv.2019.64.v1

Published 09 Jul 2019

  • Preprint

Abstract

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.

Supporting Information

Format: DOCX Size: 5.3 MB Download

How to Cite

When a peer-reviewed version of this preprint is available in the Beilstein Journals, 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

Download Citation
Download RIS (Reference Manager) Download BIB (BIBTEX)

© 2019 LE et al.; licensee Beilstein-Institut.
This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited.
The license is subject to the Beilstein Archives terms and conditions: (https://www.beilstein-archives.org/xiv/terms)

Other Beilstein-Institut Open Science Activities

Logo
Logo
Logo
Symposia