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- Title
Enantioselective Cu-catalyzed double hydroboration of alkynes to access chiral gem-diborylalkanes.
- Authors
Jin, Shengnan; Li, Jinxia; Liu, Kang; Ding, Wei-Yi; Wang, Shuai; Huang, Xiujuan; Li, Xue; Yu, Peiyuan; Song, Qiuling
- Abstract
Chiral organoborons are of great value in asymmetric synthesis, functional materials, and medicinal chemistry. The development of chiral bis(boryl) alkanes, especially optically enriched 1,1-diboron compounds, has been greatly inhibited by the lack of direct synthetic protocols. Therefore, it is very challenging to develop a simple and effective strategy to obtain chiral 1,1-diborylalkanes. Herein, we develop an enantioselective copper-catalyzed cascade double hydroboration of terminal alkynes and highly enantioenriched gem-diborylalkanes were readily obtained. Our strategy uses simple terminal alkynes and two different boranes to construct valuable chiral gem-bis(boryl) alkanes with one catalytic and one ligand pattern, which represents the simplest and most straightforward strategy for constructing such chiral gem-diborons. Optically enriched 1,1-diboron compounds are significantly underdeveloped because of the paucity of the straightforward synthetic protocols. Herein, the authors report an enantioselective copper-catalyzed cascade double hydroboration of terminal alkynes to access highly enantioenriched gem-diborylalkanes.
- Subjects
HYDROBORATION; ALKYNES; PHARMACEUTICAL chemistry; BORANES; ASYMMETRIC synthesis; ALKANES
- Publication
Nature Communications, 2022, Vol 13, Issue 1, p1
- ISSN
2041-1723
- Publication type
Article
- DOI
10.1038/s41467-022-31234-2