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<p>Ring-constrained biaryls possess unique axial chirality, but methods to synthesize them with adjustable ring sizes remain limited. We report a “twist-expand-seal” strategy for preparing a unique class of cyclic biaryls that exhibit axial chirality and conformational constraint, with tunable ring sizes. This method enables the streamlined synthesis of 9- to 14-membered cyclic biaryls, achieving yields of up to 99% and enantioselectivities of up to 99% ee (49 examples). This approach begins with enantioselective ring-opening of a “flat” biaryl-embedded lactam mediated by a bifunctional chiral <i>N</i>-heterocyclic carbene (NHC) catalyst (twist). Chain expansion is achieved via introducing alcohols of varying chain lengths (expand), and the final ring closure is accomplished through diverse C–C or C–N bond-forming reactions (seal). Scalable synthesis and subsequent ring transformations are readily achieved. This work expands the chemical space of axial chirality by enabling the versatile synthesis of diverse biaryl-bridged ring scaffolds.</p>

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Enantioselective synthesis of ring-constrained biaryls via a twist-expand-seal strategy

  • 期刊论文

  • 出版模式：

    开放获取

  • 发表日期：

    2026年7月27日

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  • Yuxing Cai,
  • Yuxuan Zhang,
  • Hanyu Gao,
  • Yong Huang

摘要

Ring-constrained biaryls possess unique axial chirality, but methods to synthesize them with adjustable ring sizes remain limited. We report a “twist-expand-seal” strategy for preparing a unique class of cyclic biaryls that exhibit axial chirality and conformational constraint, with tunable ring sizes. This method enables the streamlined synthesis of 9- to 14-membered cyclic biaryls, achieving yields of up to 99% and enantioselectivities of up to 99% ee (49 examples). This approach begins with enantioselective ring-opening of a “flat” biaryl-embedded lactam mediated by a bifunctional chiral N-heterocyclic carbene (NHC) catalyst (twist). Chain expansion is achieved via introducing alcohols of varying chain lengths (expand), and the final ring closure is accomplished through diverse C–C or C–N bond-forming reactions (seal). Scalable synthesis and subsequent ring transformations are readily achieved. This work expands the chemical space of axial chirality by enabling the versatile synthesis of diverse biaryl-bridged ring scaffolds.