4.7 Article

In Tandem Auto-Sustainable Enantioselective Heck-Matsuda Reactions Directly from Anilines

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 364, Issue 11, Pages 1863-1872

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202200205

Keywords

Enantioselective Heck reactions; arene-diazonium salts; in tandem reactions; palladium; desymmetrizations

Funding

  1. Sao Paulo Research Foundation (FAPESP) [2014/26378-2, 2014/25770-6, 2013/07600-3]
  2. Brazilian National Research Council (CNPq) [457027/2014-2, 305387/2013-8]
  3. CNPq [155377/2018-3]
  4. Coordination for the Improvement of Higher Education Personnel (CAPES)

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This study describes a method for the enantioselective Heck-Matsuda reaction of cyclic and acyclic olefins directly from anilines. The method demonstrates a broad substrate scope and high enantioselectivity and yield in the synthesis of Heck adducts.
An in tandem enantioselective Heck-Matsuda (HM) reaction of cyclic and acyclic olefins directly from anilines is described. The method relies on a process involving the progressive in situ diazotization of the starting anilines followed by a palladium-catalyzed Heck-Matsuda arylation using chiral N,N-ligands. This intermolecular enantioselective HM arylation strategy was applied to the desymmetrization of three distinct unactivated olefins as proof of concept. The method demonstrates broad substrate scope furnishing the Heck adducts in good to excellent enantiomeric ratios of up to 99:1, high diastereoselectivities (cyclopenten-3-ol with > 20:1 dr), and good overall yields of up to 82% over 2 or 3 steps.

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