4.8 Article

Pd(II)-Catalyzed Tandem Enantioselective Methylene C(sp3)-H Alkenylation-Aza-Wacker Cyclization to Access β-Stereogenic γ-Lactams

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 33, Pages 14060-14064

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202004504

Keywords

aza-Wacker cyclization; C-H activation; enantioselectivity; palladium; cascade reaction

Funding

  1. NSFC [21925109, 21772170]
  2. Outstanding Young Talents of Zhejiang Province High-level Personnel of Special Support [ZJWR0108]
  3. Fundamental Research Funds for the Central Universities [2018XZZX001-02]
  4. Zhejiang Provincial NSFC [LR17B020001]

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Herein, we describe an unprecedented cascade reaction to beta-stereogenic gamma-lactams involving Pd(II)-catalyzed enantioselective aliphatic methylene C(sp(3))-H alkenylation-aza-Wacker cyclization through syn-aminopalladation. Readily available 3,3 '-substituted BINOLs are used as chiral ligands, providing the corresponding gamma-lactams with broad scope and high enantioselectivities (up to 98 % ee).

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