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<p>Precise construction of molecular chirality is a longstanding scientific challenge in synthetic chemistry. Although methods to enantioselectively assemble consecutive carbon stereocenters are abundant, courses to establish enriched continuous heteroatomic stereocenters have acquired less attention and remain a tremendous challenge. Of those atoms in main group elements, nitrogen and boron are the most intractable ones to control their chirality. The copper-catalyzed asymmetric insertion reaction is one of the most significant transformations to construct C-B bonds in organic synthesis. Herein, we report a protocol to synthesize troublesome continuous heteroatomic stereocenters from cyclic amine boranes and diazo compounds via asymmetric B-H insertion reaction. The protocol is compatible with a wide range of amine boranes and diazo compounds, exhibiting high diastereo- and enantioselectivities. Mechanistic studies reveal a meaningful kinetic resolution pathway involved in the transformation and DFT calculations elucidate the origins of stereoselectivity and diastereoselectivity.</p>

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Catalytic asymmetric constructions of nitrogen, boron and carbon continuous stereogenic centers

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年11月12日

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  • Guan Zhang,
  • Junyi Jia,
  • Xuzhao Du,
  • Bofan Feng,
  • Kai Yang,
  • Peiyuan Yu,
  • Qiuling Song

摘要

Precise construction of molecular chirality is a longstanding scientific challenge in synthetic chemistry. Although methods to enantioselectively assemble consecutive carbon stereocenters are abundant, courses to establish enriched continuous heteroatomic stereocenters have acquired less attention and remain a tremendous challenge. Of those atoms in main group elements, nitrogen and boron are the most intractable ones to control their chirality. The copper-catalyzed asymmetric insertion reaction is one of the most significant transformations to construct C-B bonds in organic synthesis. Herein, we report a protocol to synthesize troublesome continuous heteroatomic stereocenters from cyclic amine boranes and diazo compounds via asymmetric B-H insertion reaction. The protocol is compatible with a wide range of amine boranes and diazo compounds, exhibiting high diastereo- and enantioselectivities. Mechanistic studies reveal a meaningful kinetic resolution pathway involved in the transformation and DFT calculations elucidate the origins of stereoselectivity and diastereoselectivity.