Enantioselective Synthesis of Phthalides and Isochromanones viaHeck–Matsuda Arylation of Dihydrofurans

Authors:

Kattela, Shivashankar ¹ ;  de Lucca Jr, Emilio C. ¹ ;    Correia, Carlos Roque D. ¹

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Abstract:

In  this  communication,  we  describe  the  enantioselective synthesis  of  phthalides  and  isochromanones  through  a  new palladium-catalyzed  Heck–Matsuda  arylation/NaBH4-reduction/lactonization  sequenceof  2,3-  and  2,5-dihydrofurans  in good overall yields and excellent enantioselectivities (up to 98:2 er). Thisexpeditious synthesis of chiral Heck lactol intermediates allowed thediversification of the strategy to obtain medicinally relevant chiral lactones, amines, and olefins.  The  natural product  3-butylphthalide was obtained in 3 steps with an overall yield of 33% yield in 98:2 er.

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¹  University of Campinas, Institute of Chemistry, 10384-612, São Paulo (Brazil)

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Link to full article:   https://onlinelibrary.wiley.com/doi/epdf/10.1002/chem.20180495824