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Synfacts 2025; 21(02): 169
DOI: 10.1055/a-2497-0288
Polymer-Supported Synthesis

Continuous-Flow Total Synthesis of (–)-Debromoflustramine B Using Homochiral Polymer-Supported Pd NPs

Contributor(s):
Yasuhiro Uozumi 
,
Kenji Tsukamoto
Wang J, Liang F, Dong Z, Huang J, Zhu Y *, You H *, Chen F-E *. Harbin Institute of Technology, Shenzhen, Fudan University, Shanghai, and Shenzhen Campus of Sun Yat-sen University, P. R. China
Four-Step Continuous-Flow Total Synthesis of (–)-Debromoflustramine B Using a Chiral Heterogeneous Pd NP Catalyst.

Chem. Sci. 2024;
15: 16205-16209
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Keywords

phosphoramidates - palladium nanoparticles - asymmetric catalysis - flow synthesis - asymmetric allylation

Significance

A homochiral phosphoramidate polymer was treated with [Pd(prenyl)Cl]2 to form a polymeric homochiral nanopalladium composite, polyPdNPs*. A four-step synthesis of (–)-debromoflustramine B was achieved in flow using polyPdNPs* (total 69 % yield, 86 % ee).


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Comment

Asymmetric dearomative prenylation of various indole derivatives, which is the key enantioselective step of the flow total synthesis, was examined in batch with polyPdNPs* (15 examples; up to 99 % yield, 96 % ee).


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Publication History

Article published online:
28 January 2025

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