Exploration of flow reaction conditions using machine-learning for enantioselective organocatalyzed Rauhut–Currier and [3+2] annulation sequence

Masaru Kondo, H. D. P. Wathsala, Makoto Sako, Yutaro Hanatani, Kazunori Ishikawa, Satoshi Hara, Takayuki Takaai, Takashi Washio, Shinobu Takizawa, Hiroaki Sasai

Chemical Communications · 2019 · 60 citations · 40 references

Concepts

Abstract

A highly atom-economical enantioselective organocatalyzed Rauhut-Currier and [3+2] annulation sequence has been established by using a flow system. Suitable flow conditions were explored through reaction screening of multiple parameters using machine learning. Eventually, functionalized chiral spirooxindole analogues were obtained in high yield with good ee as a single diastereomer within one minute.

References

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