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<p>[3,3]-Sigmatropic rearrangements are powerful transformations in synthetic chemistry, enabling atom-economical construction of complex architectures through stereospecific molecular skeleton reorganization. Despite their widespread utility, achieving asymmetric catalysis of [3,3]-sigmatropic rearrangements remains a substantial challenge due to the difficulty in controlling the stereochemistry and the limited availability of catalytic systems compatible with diverse substrates. Here we report a catalytic enantioselective boron-incorporating [3,3]-sigmatropic rearrangement enabling the synthesis of δ-amino acid derivatives with two adjacent stereocentres (up to 99% enantiomeric excess). This strategy combines transition-metal-catalysed carbene B–H insertion with [3,3]-sigmatropic rearrangement into a one-pot cascade sequence through a borane-traceless design.</p><p></p>

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Catalytic enantioselective tandem B–H insertion and [3,3]-sigmatropic rearrangement

  • 期刊论文

  • 发表日期：

    2026年5月4日

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  • Weici Xu,
  • Peilin Tian,
  • Liangfu Li,
  • Ming-Hua Xu

摘要

[3,3]-Sigmatropic rearrangements are powerful transformations in synthetic chemistry, enabling atom-economical construction of complex architectures through stereospecific molecular skeleton reorganization. Despite their widespread utility, achieving asymmetric catalysis of [3,3]-sigmatropic rearrangements remains a substantial challenge due to the difficulty in controlling the stereochemistry and the limited availability of catalytic systems compatible with diverse substrates. Here we report a catalytic enantioselective boron-incorporating [3,3]-sigmatropic rearrangement enabling the synthesis of δ-amino acid derivatives with two adjacent stereocentres (up to 99% enantiomeric excess). This strategy combines transition-metal-catalysed carbene B–H insertion with [3,3]-sigmatropic rearrangement into a one-pot cascade sequence through a borane-traceless design.