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Enantioselective Synthesis of Phthalides and Isochromanones via Heck–Matsuda Arylation of Dihydrofurans
Author(s) -
Kattela Shivashankar,
de Lucca Emilio C.,
Correia Carlos Roque D.
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201804958
Subject(s) - enantioselective synthesis , heck reaction , lactol , yield (engineering) , chemistry , organic chemistry , palladium , combinatorial chemistry , stereochemistry , catalysis , lactone , materials science , metallurgy
In this communication, the enantioselective synthesis of phthalides and isochromanones is described through a new palladium‐catalyzed Heck–Matsuda arylation/NaBH 4 ‐reduction/lactonization sequence of 2,3‐ and 2,5‐dihydrofurans in good overall yields and excellent enantioselectivities (up to 98:2 er). This expeditious synthesis of chiral Heck lactol intermediates allowed the diversification of the strategy to obtain medicinally relevant chiral lactones, amines, and olefins. The natural product 3‐butylphthalide was obtained in three steps with an overall yield of 33 % yield in 98:2 er.