Enantioselective Oxy‐Heck–Matsuda Arylations: Expeditious Synthesis of Dihydrobenzofuran Systems and Total Synthesis of the Neolignan (−)‐Conocarpan.

Autor:	Silva, Allan R., Polo, Ellen C., Martins, Nelson C., Correia, Carlos Roque D.
Předmět:	POLYMERIZATION CHEMICAL reactions CYCLOHEXANONES MACROMOLECULES COMPOSITE materials
Zdroj:	Advanced Synthesis & Catalysis; 1/17/2018, Vol. 360 Issue 2, p346-365, 20p
Abstrakt:	Abstract: This work discloses the first examples of an effective enantioselective oxy‐Heck–Matsuda reaction using a variety of styrenic olefins to generate chiral dihydrobenzofurans. The reaction proceeds in moderate to good yields, with high trans diastereoselectivity (up to 20:1) in enantioselectivities up to 90:10 using the N,N‐ligand pyrimidine‐bisoxazoline (PyriBox). The oxy‐Heck–Matsuda reactions were carried out under mild conditions and rather low catalyst loadings. The feasibility and practicality of the process is demonstrated by a concise total synthesis of the neolignan (−)‐conocarpan. X‐ray diffraction of an advanced brominated intermediate in the route to (−)‐conocarpan has allowed the unequivocal assignment of the absolute stereochemistry of the oxy‐Heck–Matsuda aryldihydrobenzofuran products. A rationale for the mechanism operating in these enantioselective oxy‐Heck–Matsuda reactions is also presented. [ABSTRACT FROM AUTHOR]
Databáze:	Complementary Index
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