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Radical-Based Enantioconvergent Reductive Couplings of Racemic Allenes and Aldehydes.
Shen, Haigen; Yang, Ling; Xu, Mingrui; Shi, Zhaoxin; Gao, Ke; Xia, Xiaowen; Wang, Zhaobin.
Afiliación
  • Shen H; Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry, School of Science and Research Center for Industries of the Future, Westlake University, 310024, Hangzhou, China.
  • Yang L; Institute of Natural Sciences, Westlake Institute for Advanced Study, 310024, Hangzhou, China.
  • Xu M; Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry, School of Science and Research Center for Industries of the Future, Westlake University, 310024, Hangzhou, China.
  • Shi Z; Institute of Natural Sciences, Westlake Institute for Advanced Study, 310024, Hangzhou, China.
  • Gao K; Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry, School of Science and Research Center for Industries of the Future, Westlake University, 310024, Hangzhou, China.
  • Xia X; Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry, School of Science and Research Center for Industries of the Future, Westlake University, 310024, Hangzhou, China.
  • Wang Z; Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry, School of Science and Research Center for Industries of the Future, Westlake University, 310024, Hangzhou, China.
Angew Chem Int Ed Engl ; : e202413198, 2024 Sep 02.
Article en En | MEDLINE | ID: mdl-39221920
ABSTRACT
Transition metal-catalyzed radical-based enantioconvergent reactions have become a powerful strategy to synthesize enantiopure compounds from racemic starting materials. However, existing methods primarily address precursors with central chirality, neglecting those with axial chirality. Herein, we describe the enantioconvergent reductive coupling of racemic allenes with aldehydes, facilitated by a photoredox, chromium, and cobalt triple catalysis system. This method selectively affords one product from sixteen possible regio- and stereoisomers. The protocol leverages CoIII-H mediated hydrogen atom transfer (MHAT) and Cr-catalyzed radical-polar crossover for efficient stereoablation of axial chirality and asymmetric addition, respectively. Supported by mechanistic insights from control experiments, deuterium labeling, and DFT calculations, our approach offers synthetic chemists a valuable tool for creating enantioenriched chiral homoallylic alcohols, promising to advance radical-based strategies for synthesizing complex chiral molecules.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2024 Tipo del documento: Article País de afiliación: China Pais de publicación: Alemania
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
Buscar en Google

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2024 Tipo del documento: Article País de afiliación: China Pais de publicación: Alemania