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Selective Hydroboration-Oxidation of Terminal Alkenes under Flow Conditions.

ABSTRACT: An efficient flow process for the selective hydroboration and oxidation of different alkenes using 9-borabicyclo(3.3.1)nonane (9-BBN) allows facile conversion in high productivity (1.4?g?h-1 ) of amorpha-4,11-diene to the corresponding alcohol, which is an advanced intermediate in the synthesis of the antimalarial drug artemisinin. The in situ reaction of borane and 1,5-cyclooctadiene using a simple flow generator proved to be a cost efficient solution for the generation of 9-BBN.

SUBMITTER: Elsherbini M

PROVIDER: S-EPMC7540268 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

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Selective Hydroboration-Oxidation of Terminal Alkenes under Flow Conditions.

Elsherbini Mohamed M Huynh Florence F Dunbabin Alice A Allemann Rudolf K RK Wirth Thomas T

Chemistry (Weinheim an der Bergstrasse, Germany) 20200806 50

An efficient flow process for the selective hydroboration and oxidation of different alkenes using 9-borabicyclo(3.3.1)nonane (9-BBN) allows facile conversion in high productivity (1.4 g h<sup>-1</sup> ) of amorpha-4,11-diene to the corresponding alcohol, which is an advanced intermediate in the synthesis of the antimalarial drug artemisinin. The in situ reaction of borane and 1,5-cyclooctadiene using a simple flow generator proved to be a cost efficient solution for the generation of 9-BBN. ...[more]

PMID: 32329919

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