Stereoselective rhodium-catalyzed reaction of allenes with organoboronic reagents for diversified branched 1,3-alkadienes

Weiyi Wang, Shichao Hong, Wenxiang He, Xue Zhang (), Hui Qian () and Shengming Ma ()
Additional contact information
Weiyi Wang: 220 Handan Lu
Shichao Hong: 220 Handan Lu
Wenxiang He: 220 Handan Lu
Xue Zhang: 345 Lingling Lu
Hui Qian: 220 Handan Lu
Shengming Ma: 220 Handan Lu

Nature Communications, 2024, vol. 15, issue 1, 1-11

Abstract: Abstract The terminal isoprene unit, as the simplest branched 1,3-diene unit, exists in a wide range of natural products and bioactive molecules. Herein, we report a stereoselective rhodium-catalyzed reaction of allenes with readily available methyl pinacol boronic ester, providing a straightforward approach to isoprene derivatives with a very high E-stereoselectivity. Its synthetic potential has been illustrated by a concise synthesis of natural product schinitrienin. Such a protocol can be easily extended to aryl and alkenyl boronic reagents affording 2-aryl or -alkenyl substituted 1,3-dienes, which are also of high importance in organic synthesis but remain challenging for their selective synthesis, with a remarkable stereoselectivity. A series of deuterium-labeling experiments indicate a unique mechanism, which involves reversible β-H elimination as well as hydrometalation and isomerization of the allylic rhodium species.

Date: 2024
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DOI: 10.1038/s41467-024-52209-5

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